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 .
Claim Interpretation
Independent method claim 1, dependent method claim 4 and composition claim 36, recite clauses, following respective chemical structure or formula components, beginning “may be” which render the clauses ambiguous and indefinite, including: claim 1: “which may be saturated or contain one or more double bonds and/or triple bonds”, “which may contain one or more functional groups”, and “may be a double or single bond”; and each of claims 4 and 36: “which may be saturated or contain one or more double bonds and/or triple bonds”, and “which may be saturated or contain one or more double bonds, respectively.
Thus these claims are each interpreted as respectively reciting structure or formula which optionally are saturated, contain one or more functional groups and/or contain one or more double and/or triple bonds, respectively.
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.
Claims 1-9,11,13,15-18,21-22,24,26 and 36 are rejected under 35 U.S.C. 112(b) as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor regards as the invention.
The claims include clauses beginning “may be” which render the clauses ambiguous and indefinite, including: claim 1: “which may be saturated or contain one or more double bonds and/or triple bonds”, “which may contain one or more functional groups”, and “may be a double or single bond”; and each of claims 4 and 36: “which may be saturated or contain one or more double bonds and/or triple bonds”, and “which may be saturated or contain one or more double bonds, respectively.
In each of claims 2 and 3, “the triazine-based acylating agent” (singular) lacks antecedent basis, being inconsistent with preceding recitation in claim 1 of “one or more…agents” (singular or plural), and “triazine-based acylating agents” (plural) also lacks antecedent basis, again being inconsistent with preceding recitation in claim 1 of “one or more…agents” (singular or plural), (were the claims intended to recite each of the one or more triazine agents comprising the respective, recited formulas?).
In claim 3, “each of said compounds” also lacks antecedent basis (was reference to formulae instead suggested?).
In each of claims 4, 7 and 8 “the triazine-based acylating agent of formulas (3), (4), (5), (6), and (7)” (singular) again lacks antecedent basis, being inconsistent with preceding recitation in claim 1 of “one or more…agents” (singular or plural), with claims 1 and 2 also lacking recitation of “formulas (4), (5), (6), and (7)” (it is suggested that claims 4, 7 and 8 be made to be dependent on claim 3 which does recite these formulas).
In claim 9, it is unclear what is meant by “of the lysosphingolipid of formula (2)”, and it is unclear whether such clause refers only to when the salt is selected from a perchlorate salt, or pertains to any of the salt selection options of the Markush group.
In claim 11, “consisting of from” is grammatically confusing (it is suggested that “from” be deleted); and,
“the use of a base” is vague and ambiguous as it is unclear as to whether such use relates to the recited “reacting and producing” step introduced in claim 1, or to a separate method step, and unclear as to whether the recited “base” is introduced or mixed with the “one or more triazine-based acylating agents” introduced in claim 1, or alternately is utilized before or after reaction with such acylating agent(s).
In claim 13, “wherein the polar solvent” is inconsistent with preceding recitation of “one or more polar solvents” and it is unclear whether “the polar solvent” is referring back to “a polar solvent” or to one or more polar solvents”; and,
“the polar solvent is” (singular) is inconsistent with preceding recitation of “one or more polar solvents” and the claim is unclear whether the Markush group selection options pertain to each of the one or more polar solvents for the option of there being more than one solvent;
additionally, “the use of a solvent” is vague and ambiguous as it is unclear as to whether such use relates to the recited “reacting and producing” step introduced in claim 1, or to a separate method step, and unclear as to whether the recited “solvent” is introduced or mixed with the “one or more triazine-based acylating agents” introduced in claim 1, or alternately is utilized before or after reaction with such acylating agent(s).
In claim 16, each recitation of “the stereochemical configuration” lacks antecedent basis.
In claim 21, “W of the lysosphingolipid of formula (2), (14) or (15)” lacks antecedent basis, (changing the claim dependency to claim 15 where formula (14) or (15) is introduced is suggested).
In claim 24, “the following steps…or the combination thereof” is non-idiomatic or grammatically confusing (it is suggested that “or the combination thereof” be deleted), and plural subsequent recitations of “the combination thereof” are similarly confusing and redundant, it being suggested that each of such recitations be deleted; and, the meaning of “are performed in a non-halogenated solvent” is unclear (“…comprise the carboxylic acid and organic base being dissolved in a non-halogenated solvent” is suggested).
In claim 26, “are performed in a non-halogenated solvent” is again unclear (“…comprise the carboxylic acid and organic base being dissolved in the same non-halogenated solvent” is suggested).
Also, in claim 36, the scope and meaning of “or a combination thereof” is ambiguous and unclear as recitation of only a single formula (3) precedes such clause, (a combination of what formula or formula components?)
Allowable Subject Matter
Claims 1-9,11,13,15-18,21-22,24,26 and 36 would be allowable if rewritten or amended to overcome the rejections under 35 U.S.C. 112(b) set forth in this Office action.
Independent method claim 1 would distinguish and be non-obvious over all of the prior art in view of recitation of: A method for the production of a sphingolipid of formula (1): wherein W is hydrogen or a glycosyl moiety, R¹ is H, aryl, or a C1-50 alkyl,… R² is H or -OR⁵, wherein R⁵ is selected from hydrogen, a substituted or unsubstituted C₁-₆ alkyl, or a substituted or unsubstituted C₁-₆ acyl,
the bond === may be a double or a single bond when R² is H, or is a single bond when R² is - OR⁵,
R³ is H, a substituted or unsubstituted C₁-₆ alkyl, or a substituted or unsubstituted C₁-₆ acyl, R⁴ is selected from hydrogen, a substituted or unsubstituted aryl, a heteroalkyl, a substituted or unsubstituted C1-31 alkyl, the method comprising:
reacting a lysosphingolipid of formula (2):… wherein W, the bond = , R¹, R² and R³ are as defined as for the sphingolipid of formula (1), with one or more triazine-based acylating agents of formula (3):… wherein
represents a conjugated system of bonds such that either two or three double bonds are present in the ring; Y is selected from C(O-C(=O)R⁴), or C(=O), Xᵃ is selected from N, NR⁶, or N(C(=O)R⁴) Xᵇ is selected from N, or NR⁶ Z is selected from C(=O), or C(OR⁶).
The closest prior art of record with respect to claim 1 regarding methods for production of lysosphingolipids, generally and sphingolipids in particular includes Ito et al PGPUBS Document US 2002/0086410, Dela Valle et al patent 5,519,007, Holler patent 5,532,141, Japanese patent publication JP 3625244 A and the accompanying English translation, the publication by Gerrit van Meerl et al entitled "Sphingolipid Transport: Rafts and Translocators", and, the publication by Beata Kolesinska, "The umpolung of substituent effect in nucleophilic aromatic substitution. A new approach to the synthesis of N,N-disubstituted melamines under mild reaction conditions".
Such prior art cumulatively teaches production of the claimed sphingolipid formula including by reacting a lysosphingolipid of the claimed formula and acylation.
However, no combination of the prior art suggests such production also including the reacting being with a triazine-based acylating agent having a formula wherein the triazine ring includes a “Y” component being selected from C(O-C(=O)R⁴), or C(=O).
The closest prior art of record also includes two Non patent Literature publications which were considered in the 371 Stage of Prosecution concerning general state of the art regarding sphinigolipid formulas and methods of preparation: SUZUKI MASAHIRO ET AL: "Novel organogelators based on phytosphingosine",TETRAHEDRON LETTERS, ELSEVIER, AMSTERDAM NL, vol. 57, no. 25, 13 May 2016 (2016-05-13), pages 2807-2810, and SON SANG-HYUN ET AL: "Syntheses of lactosyl ceramide analogues carrying novel bifunctional BODIPY dyes directed towards the differential analysis of multiplexed glycosphingolipids by MS/MS using iTRAQ", CHEMICAL COMMUNICATIONS, vol. 50, no. 23, 1 January 2014 (2014-01-01), pages 3010-3013. However such prior art also lacks a teaching of reacting of a lysosphingolipid, using a triazine-based acylating agent having a formula wherein the triazine ring includes a “Y” component being selected from C(O-C(=O)R⁴), or C(=O).
Dependent method claims 2-9, 11, 13, 15-18, 21-22, 24, and 26 would also distinguish and be non-obvious in view of their respectively being dependent on claim 1, which distinguishes and non-obvious.
Independent method claim 36 would distinguish and be non-obvious over all of the prior art in view of recitation of: A triazine based acylating agent of formula (3), or a combination thereof:… wherein
represents a conjugated system of bonds such that either two or three double bonds are present in the ring; Y is selected from C(O-C(=O)R⁴), or C(=O), Xª is selected from N, NR⁶, or N(C(=O)R⁴) Xᵇ is selected from N, or NR⁶ Z is selected from C(=0), or C(OR⁶)… provided that:
when Y is C(O-C(=O)R⁴), Z is C(OR⁶), Xª and Xᵇ are N, and three double bonds are present in the ring, or
when Y is C(O-C(=O)R⁴), Z is C(=O), one of Xª and Xᵇ is N and the other group is NR⁶, and two double bonds are present in the ring, or
when Y is C(=O), Z is C(OR⁶), Xᵃ is N(C(=O)R⁴), Xᵇ is N, and two double bonds are present in the ring.
The closest prior art with respect to the triazine composition of claim 36 is represented by the Non-Patent Literature publication of Ahmed Raza, "Trifunctional covalent triazine and carbonyl based polymer for one-pot organic transformation", published in Reactive and Functional Polymers, and by D’Alelio patent 3,244,709 and Japanese patent publication JP 2868098 and the accompanying English translation which cumulatively teach the triazine based acylating agent of formula (3), however lacking a teaching or suggestion of a conjugated system of bonds such that either two or three double bonds are present in the ring; Y is selected from C(O-C(=O)R⁴), or C(=O), Xª is selected from N, NR⁶, or N(C(=O)R⁴) Xᵇ is selected from N, or NR⁶ Z is selected from C(=0), or C(OR⁶)… provided that:
when Y is C(O-C(=O)R⁴), Z is C(OR⁶), Xª and Xᵇ are N, and three double bonds are present in the ring, or
when Y is C(O-C(=O)R⁴), Z is C(=O), one of Xª and Xᵇ is N and the other group is NR⁶, and two double bonds are present in the ring, or
when Y is C(=O), Z is C(OR⁶), Xᵃ is N(C(=O)R⁴), Xᵇ is N, and two double bonds are present in the ring.
Conclusion
The prior art made of record and not relied upon is considered pertinent to applicant's disclosure.
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JWD
09/15/2026
/JOSEPH W DRODGE/Primary Examiner, Art Unit 1773
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