DETAILED ACTION
This Office Action is the result of a new line of rejection provided by evidence that was overlooked in the now rescinded allowance filed March 10th, 2026. The new grounds of rejection to claims 2 and 24 is based on exemplary language used in the claims. Objections to claims 3 and 19 for confusing claim language,
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 .
Priority
The present application is the U.S. National Stage Application, pursuant to 35 U.S.C.371, of PCT International Application No. PCT/EP2020/078600 filed October 10, 2020 which claims priority to Foreign Patent No. EP19203823 filed October 17, 2019.
Status of the Claims
Claims 1-3 and 16-26 are pending and examined on their merits.
Claim Objections
Claim 3 is confusing because the diastereomeric salt compounds of claim 1 are clearly larger than and different from the moieties recited in line 3 of claim 3. That these moieties are intended to be alternative embodiments of variable moiety "Ar" where Ar is an unsubstituted or substituted aromatic radical is evident, however, from the words “in which * represents the cite of attachment” in line 4 of the claim and by the fact that the claim recites similar language for other Markush groups of Ar alternatives in the same claim.
Claim 19 is somewhat confusing due to the presence of an additional period in the middle of the claim.
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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.
Claims 2 and 24 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.
Claim 2 and each of the dependent claims are vague and indefinite due to several different instances where a generic limitation is recited and immediately followed by exemplary language that is in turn immediately followed by more specific embodiments that fall within the scope of the generic limitation. This use of exemplary language throughout claim 2 makes the metes and bounds of what is encompassed by claim 2 indefinite because it’s unclear whether the specific examples that follow the exemplary language are necessarily required by the claim or, if the more specific limitations are not necessarily required, under what circumstances the more specific limitations may be ‘preferred’ for the claimed invention. See MPEP 2173.05(d). A review of the specification in each instance regarding the recited limitations fails to clarify the issue regarding whether the more specific embodiments recited in the claim following exemplary language are necessarily required by the claim, and if not, under what circumstances the more specific embodiments may be preferred.
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Independent claim 1 is directed to diastereomeric salt of the formula (Va), (Vb), (Vc) and/or (Vd), where the structural formula for each of the different diastereomeric salts is shown in the claim. Each of the formulae recites a variable “Ar” at multiple points where “Ar” is required to be an unsubstituted or substituted aromatic or heteroaromatic radical. Claim 2 depends from claim 1 and further limits the claim by defining what moieties may be present as the variable “Ar”. In doing so, claim 2 recites numerous instances of exemplary language that serve to make the metes and bounds of what is required by the claim unclear and confusing.
Exemplary Language – Examples of exemplary language in claim 2 include the following:
Generic Limitation:
Exemplary Language:
Species:
(i) alkyl radical
for example
methyl, ethyl, propyl
(ii) ether group
for example
O-methyl, O-ethyl, O-phenyl
(iii) amide group
for example
“…-NHCOR…or -NRCOR…or -CONHR…or -CONRR’”
(iv) cyclic amides
such as
3-oxomorpholin-4-yl, 2-oxopiperidin-1-yl
(v) cyclic amides; or 3-oxomorpholin-4-yl, 2-oxopiperidin-1-yl
“which may in turn be substituted, and further wherein substitution patterns may differ widely; for instance, up to 5 different substituents are theoretically possible, but preference is generally given to”
monosubstituted Ar radicals
(vi) substituted heteroaromatic radical
“such as, preferably,”
pyridine, pyrazine
(vii) a polycyclic aromatic hydrocarbon
for example
substituted naphthalene, anthracene, quinoline
Regarding (v) above, the phrase “…wherein R1, R2, R3, R4, R5 are each a hydrogen or alkyl radical…or a halogen atom…or an ether group…or a nitro group, or a cyano group, a CF3 group, or an amide group…or cyclic amides…which may in turn be substituted, and further wherein substitution patterns may differ widely; for instance, up to 5 different substituents are theoretically possible, but preference is generally given to the monosubstituted Ar radicals” is problematic due to the exemplary language “…but preference is generally given to the monosubstituted Ar radicals”. This phrase expressly indicates that monosubstituted Ar radicals (i.e., where only one of R1, R2, R3, R4 and R5 is other than hydrogen) are given preference or required under at least certain circumstances and not given preference or not present at other times (e.g., “preference is generally given”). The instant disclosure, however, does not clearly delineate the circumstances under which preference for monosubstituted radicals is given and when it is not. For example, the specification refers to “monosubstituted Ar radicals” only a few times and never appears to delineate those circumstances for when the monosubstituted Ar radicals are required for the invention and those instances where they are excluded from the invention (e.g., page 15, lines 2-3; page 37, lines 1-2; page 42, lines 12-13; page 59, lines 16-17; page 94, lines 6-7; etc.). Therefore, one of skill in the art would not be able to determine what diastereomeric salt compounds are encompassed by claim 2 in a given circumstance and which ones are excluded by the claim language in that same circumstance.
Regarding (i) above, the first use of exemplary language is the recitation of “for example” following the generic language of “an alkyl radical” and prior to the recitation of the specific embodiments, “methyl, ethyl, propyl”. The instant disclosure describes the term “alkyl radical” as encompassing a methyl, ethyl or propyl radical, but does not do so in a limiting way (e.g., page 14, lines 21-22; page 36, lines 7-8; page 42, lines 5-6; etc.). One of skill in the art, however, could readily envision other possibilities than just those disclosed in the instant disclosure (e.g., butyl, pentyl, etc.). For example, the specification teaches at page 13 that substituents can include C1-C6 alkyl groups (e.g., page 13, line 20; etc.). On the other hand, these three groups are the only alternatives of an alkyl radical that are expressly named in the disclosure, implying that their explicit recitation in the claim may actually be intended to be limiting in some manner. Therefore, it is not clear whether the embodiments following the recitation of “for example” are necessarily limiting for the generic recitation of “an alkyl radical” as recited in claim 2, and if not, under what circumstances those embodiments may be preferred in some manner.
Regarding (ii) above, the recitation of the exemplary language “for example” following the generic term “ether group” is followed by the recitation of the specific types of ether groups “O-methyl, O-ethyl, “O-phenyl”, presumably in the alternative. The instant disclosure describes the term “ether group” as encompassing O-methyl, O-ethyl or O-phenyl embodiments, but does not do so in a limiting manner (e.g., see page 14, lines 22-23; page 36, lines 8-9; page 42, lines 7-8; etc.). One of skill in the art, however, could readily envision other possible ether groups that could serve as “Ar” in the compounds of claim 2 (e.g., O-propyl, etc.). On the other hand, these three alternatives are the only alternatives of an ether group that are expressly named in the disclosure, implying that their explicit recitation in the claim might actually be intended to be limiting in some manner. Therefore, it is not clear whether the embodiments following this recitation of “for example” are necessarily limiting for the generic recitation of an “ether group” in claim 2, and if not, under what circumstances those embodiments may be preferred in some manner.
Regarding (iii) above, the recitation of the exemplary language “for example” following the generic term “amide group” is followed by the recitation of the specific cyclic amides “…-NHCOR…or -NRCOR…or -CONHR…or -CONRR’”. The instant disclosure describes the term “amide group” as encompassing compounds of the formulas NHCOR, NRCOR, CONHR and CONRR’, but in a non-limiting, exemplary way (e.g., page 13, line 20-page 14, line 2; page 14, lines 24-26; page 36, lines 10-14; page 42, lines 8-10; etc.). One of skill in the art could envision other amide groups that could work as “Ar”, such as embodiments where variable “R” in NHCOR, NRCOR, CONHR or CONRR’ is other than a methyl, ethyl or phenyl group (e.g., a propyl group). On the other hand, these four structural alternatives are the only alternatives of an amide group that are expressly named in the disclosure, implying that their explicit recitation in the claim might actually be intended to be limiting in some manner. Therefore, it is not clear whether the embodiments following this recitation of “for example” are necessarily limiting for the generic recitation of an “amide group” in claim 2, and if not, under what circumstances those embodiments may be preferred in some manner over other possible embodiments.
Regarding (iv) above, the recitation of the exemplary language “such as” following the recitation of the generic term “cyclic amides” is immediately followed by the recitation of the specific embodiments “3-oxomorpholin-4-yl” and “2-oxopiperidin-1-yl”. The only two specific cyclic amides described in the instant disclosure are 3-oxomorpholin-4-yl and 2-oxopiperidin-1-yl, strongly implying that their recitation in claim 2 may be limiting. On the other hand, the instant disclosure defines the term “cyclic amide” as encompassing compounds other than just 3-oxomorpholin-4-yl and 2-oxopiperidin-1-yl in that the cyclic amides of the invention can be further substituted (e.g., page 14, lines 1-2: “which may in turn be substituted”; page 14, line 26-page 15, line1; etc.), which implies that the recitation of 3-oxomorpholin-4-yl and 2-oxopiperidin-1-yl is not actually limiting, at least all of the time. Thus, it is not clear whether the recitation of 3-oxomorpholin-4-yl and 2-oxopiperidin-1-yl following the exemplary language “such as” is further limiting for claim 2, making the metes and bounds of the claim indefinite.
Regarding (vi) above, the recitation of the exemplary language “such as, preferably,” following the generic recitation of the term “heteroaromatic radical” is immediately followed by the recitation of the specific embodiments pyridine and pyrazine. The instant disclosure describes the generic term as encompassing both pyridine and pyrazine, but only in an exemplary, non-limiting manner (e.g., “such as”, “preferably”; page 15, lines 3-5; page 37, lines 2-3; page 42, lines 13-15; etc.). Moreover, the instant disclosure does not describe under what circumstances pyridine or pyrazine would be the ‘preferred’ embodiment of a heteroaromatic radical for use as a substituent in Ar for the claimed diastereomeric salt compounds. In addition, one of skill in the art can readily envision other heteroaromatic compounds other than pyridine or pyrazine. On the other hand, these two specific compounds are the only alternatives of a heteroaromatic radical that are expressly named in the disclosure, implying that their explicit recitation in the claim might actually be intended to be limiting in some manner. Therefore, it is not clear whether the terms pyridine and pyrazine are necessarily limiting for claim 2 as written, and if not, under what circumstances the two compounds might be preferred embodiments.
Regarding (vii) above, the recitation of the exemplary language “for example” following the generic recitation of the term “polycyclic aromatic hydrocarbon” is immediately followed by the recitation of the specific embodiments of substituted naphthalene, anthracene and quinoline. The instant disclosure describes the term “polycyclic aromatic hydrocarbon” as encompassing a substituted naphthalene, anthracene or quinoline, but in a non-limiting way (e.g., “for example”; page 15, lines 5-6; page 37, lines 4-5; page 42, lines 15-16). In addition, the specification does not indicate under what circumstances those specific embodiments might be the ‘preferred’ embodiments of polycyclic aromatic hydrocarbons as recited in claim 2. Moreover, one of skill in the art could readily envision other polycyclic aromatic hydrocarbons that could function as Ar in the claimed compounds (e.g., an unsubstituted naphthalene, etc.). On the other hand, these three specific compounds are the only alternatives of polycyclic aromatic hydrocarbon that are expressly named in the disclosure, implying that their explicit recitation in the claim might actually be intended to be limiting in some manner. Therefore, it is not clear whether the recitation of a substituted naphthalene, anthracene and quinoline after the recitation of “for example” in claim 2 necessarily limits the choices for polycyclic aromatic hydrocarbons to those specific embodiments. If those embodiments are found to be exemplary, then it is not clear under what circumstances those recited embodiments would be preferred over other possible polycyclic aromatic hydrocarbons for the Ar moiety in the compounds of claim 2.
Each instance of exemplary language outlined above (i.e., (i)-(vii)) makes the metes and bounds of claim 2 indefinite by making it unclear whether the specific embodiments following the exemplary language are necessarily required for the claimed invention. In each case, the specific embodiments recited after the exemplary language are disclosed in the instant specification as at least preferred embodiments by virtue of the fact that they are described by name as exemplary of a generic moiety (e.g., methyl, ethyl and propyl as examples of alkyl radicals). The specification fails to make clear, however, whether those preferred embodiments are necessarily limiting for the claimed invention regarding the generically-recited moiety or whether they are merely preferred embodiments. In addition, even if one considers the specifically-recited embodiments as merely exemplary in nature, which is not conceded here, the specification does not describe the fact patterns or circumstances under which the specifically-recited embodiments are preferred or otherwise required for the claimed invention. Note that this is particularly true in claim 2 regarding the language “…but preference is generally given to the monosubstituted Ar radicals” where the specification fails to delineate those instances where preference is given, or not given, to the monosubstituted Ar radicals. Given this lack of help from the instant disclosure, and given that additional embodiments can be envisioned by the skilled artisan for each of the generically-recited moieties for the compounds of claim 2, it is apparent that the cited exemplary language from claim 2 makes the metes and bounds of what is necessarily encompassed by the claim indefinite.
Claim 24 is directed to a method of preparing the compound of formula (Ia) and recites five steps towards achieving that goal (i.e., steps (i)-(v)). Step (ii) of the claim is directed to the conversion of the diastereomeric salts of formula (Va) and/or (Vc) obtained in step (i) to the compound of formula (IVa), which is then reacted with an orthoester under acidic catalysis conditions to obtain the compound of formula (VIIa) in step (iii) of the claim.
The issue with step (ii) of claim 24 is the parenthetical recitation of a limitation that the conversion of the diastereomeric salt compounds of formula (Va) and/or (Vc) to the compound of formula (IVa) is performed by treatment of those compounds with a base. The use of the parentheses in combination with the exemplary term “preferably” strongly implies that this portion of step (ii) in claim 2 is optional or merely a preferred embodiment of the claimed method. For example:
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The relevant portion of the specification reads as follows (page 25-27).
“In the next step, the diastereomeric salt is treated with a base, and the solvent is removed. The solvent is removed by methods known to the person skilled in the art, for example by distillative removal. For preparation of the chiral compounds (IVa) and (IVb), the diastereomeric salt of the general formula (Va), (Vb), (V c) or (V d) has to be treated with a base; distillative removal of the organic solvent precipitates the target molecule (IV a) or (IVb) out of the solution, which is isolated – for example by filtering-off and washing on the filter - and the respective tartaric ester of formula (Illa) or (Illb) remains in solution in the form of a salt.”
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Suitable bases in the context of the present invention are inorganic and organic bases. In the case of inorganic bases, it is possible to use ammonia, aqueous sodium hydroxide solution, lithium hydroxide, potassium hydroxide, ammonium carbonate, sodium carbonate, potassium carbonate, lithium carbonate, ammonium hydrogencarbonate, sodium hydrogencarbonate, potassium 5 hydrogencarbonate, sodium phosphate, potassium phosphate, ammonium phosphate. However, preference is given to using sodium hydroxide, sodium phosphate or potassium phosphate. Particular preference is given to using sodium phosphate or potassium phosphate. It is important to emphasize that the inorganic bases may be used either in anhydrous form or in the form of their hydrates; for example, sodium phosphate (anhydrous) and sodium phosphate hydrate may be used successfully. Organic bases used may be aliphatic or aromatic bases, for example triethylamine, imidazole, Nmethylimidazole, Huinig's base, pyridine, DBU.
This portion of the original disclosure expressly states that for preparation of the chiral compounds (IVa) and (IVb), the diastereomeric salt of the general formula (Va), (Vb), (Vc) or (Vd) has to be treated with a base (e.g., page 23, lines 14-15). This statement does not appear to be contradicted anywhere else in the instant disclosure and is reasonably construed as an admission by Applicant that this step, treatment of the diastereomeric salt of formula (Va) and/or (Vc) with a base to obtain the compound of formula (IVa), as recited in step (ii) of claim 24, is a critical step of the claimed invention. See MPEP 2172.01 regarding unclaimed essential subject matter.
Notably, even if one doesn’t interpret the specification as requiring the treatment of (Va) and/or (Vc) with a base to obtain compound (IVa), it is apparent that the specification does not appear to teach under which conditions this treatment step is the ‘preferred’ embodiment, and when it is not. Thus, the instant disclosure doesn’t clarify under what conditions the step of treating with a base is not ‘preferred’ or required. Based on the fact pattern as outlined above, it is apparent that claim 24 uses exemplary language (e.g., the parenthetical use of the term “preferably”) to make optional a limitation that Applicant has apparently indicated in the disclosure is an essential step for the claimed method. Thus, based on the manner claim 24 is written and the contradiction between the claimed method and the teachings of the instant disclosure, one of skill in the art would not be able to determine the scope of what is necessarily required by the claim and what is not, making the metes and bounds of the claim indefinite.
Conclusion
Claims 2 and 24-26 are rejected.
Claims 1, 3 and 16-23 are free from the art.
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/P.R.G./Examiner, Art Unit 1629
/JEFFREY S LUNDGREN/Supervisory Patent Examiner, Art Unit 1629
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