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 .
Information Disclosure Statement
Acknowledgment is made of Applicant’s Information Disclosure Statement (IDS) form PTO 1449.These IDS has been considered.
Examiner’s Note
The Examiner has pointed out particular references contained in the prior art of record within the body of this action for the convenience of the Applicant. Although the specified citations are representative of the teachings in the art and are applied to the specific limitations within the individual claim, other passages, paragraph and figures may apply. Applicant, in preparing the response, should consider fully the entire reference as potentially teaching all or part of the claimed invention, as well as the context of the passage as taught by the prior art or disclosed by the Examiner.
Claim Rejections - 35 USC § 102
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.
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.
Claims 1-2 are rejected under 35 U.S.C. 102(a1) as being anticipated by (US 9,796,721 B2) (Acerta Pharma B.V.) (hereinafter "Acerta") [cited in the IDS filed by the applicant].
As per claim 1, Acerta discloses a method for obtaining a Raman spectrum of a sample, the method comprising: providing a sample; depositing one or more aromatic additives onto the sample; and c obtaining a Raman spectrum of the sample (crystalline (S)-4-(8-amino-3-( 1-(but-2-ynoyl)pyrrolidin-2-yl)imidazo[1,5-a]pyrazin-1-yl)-N-(pyridin-2-yl)benzamide gentisate was produced by mixing free base of Formula I and gentisic acid, and has a Raman spectrum with at least five characteristic peaks, where gentisic acid or 2,5-dihydroxybenzoic acid is the aromatic benzoic acid derivative; column 18, lines 1-1 O; column 104, lines 40-67).
As per claim 2, Acerta discloses the method of claim 1, and Acerta further discloses wherein the one or more aromatic additives have an absorbance ranging from about 250 nm to about 500 nm (crystalline (S)-4-(8-amino-3-(1-(but-2-ynoyl)pyrrolidin-2-yl)imidazo[ 1,5-a Jpyrazin-1-yl)-N-(pyridin-2-yl)benzamide gentisate was produced by mixing free base of Formula I and gentisic acid, where gentisic acid or 2,5-dihydroxybenzoic acid is the aromatic benzoic acid derivative comprising phenyl ring and is expected to have at least a residual absorbance at 250 nm in standard aqueous conditions, the applicants do not disclose the value of expected absorbance and conditions of spectroscopy performance; column 18, lines 1-10; column 104, lines 40-67).
Claim Rejections - 35 USC § 103
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.
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 of this title, 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) 3-10, 13-14, 18, 20 and 21-23 is/are rejected under 35 U.S.C. 103 as being unpatentable over Acerta.
As per claim 3, Acerta discloses the method of claim 2, and Acerta further discloses the one or more aromatic (crystalline (S)-4-(8-amino-3-(1-(but-2-ynoyl)pyrrolidin-2-yl)imidazo[ 1,5-a ]pyrazin-1-yl)-N-(pyridin-2-yl)benzamide gentisate was produced by mixing free base of Formula I and gentisic acid, where gentisic acid or 2,5-dihydroxybenzoic acid is the aromatic benzoic acid derivative comprising phenyl ring and is expected to have at least a residual absorbance at 250 nm in standard aqueous conditions, the applicants do not disclose the value of expected absorbance and conditions of spectroscopy performance; column 18, lines 1-10; column 104, lines
40-67), and in a separate embodiment Acerta further discloses wherein the compound comprises a matrix-assisted laser desorption/ionization MALDI matrix (compound of Formula 1 was mixed with succinic acid, characteristic Raman peaks for the acetone
solvate of the succinic acid co-crystal of Formula 1 were observed, where succinic acid is the MALDI matrix, as disclosed in claim 4 of the instant application; column 113, lines 25-45; column 114, lines 35-40).
It would have been obvious to a person of ordinary skill in the art, at the time of the invention, to have modified the method, as previously disclosed by Acerta, in order to have provided for wherein the compound comprises a matrix-assisted laser desorption/ionization MALDI matrix, as previously disclosed by Acerta in a separate
embodiment (column 113, lines 25-45; column 114, lines 35-40), for providing the compound in the form of mixed succinic acid salt and gentisic acid salt to improve solubility and oral bioavailability of the compound as BTK inhibitor designed for treatment of adult humans (column 25, lines 25-45). Further, provided that in both embodiments Acerta discloses salts of the same compound, where the compound
is designed as BTK inhibitor for treatment of adult humans (column 18, lines 1-10; column 25, lines 25-45; column 104, lines 40-67; column 113, lines 25-45; column 114, lines 35-40), the modification to Acerta's method, of providing for wherein the compound comprises a matrix-assisted laser desorption/ionization MALDI matrix, would provide the benefit of providing the compound in the form of mixed succinic acid salt and gentisic acid salt to improve solubility and oral bioavailability of the compound as BTK inhibitor designed for treatment of adult humans (column 25, lines 25-45).
As per claim 4, Acerta discloses the method of claim 3, and in a separate embodiment Acerta further discloses wherein the MALDI matrix is succinic acid (compound of Formula 1 was mixed with succinic acid, characteristic Raman peaks for the acetone solvate of the succinic acid co-crystal of Formula 1 were observed; column 113, lines 25-45; column 114, lines 35-40).
It would have been obvious to a person of ordinary skill in the art, at the time of the invention, to have modified the method, as previously disclosed by Acerta, in order to have provided for wherein the MALDI matrix is succinic acid, as previously disclosed by Acerta in a separate embodiment (column 113, lines 25-45; column 114, lines 35-40), for providing the compound in the form of mixed succinic acid salt and gentisic acid salt to improve solubility and oral bioavailability of the compound as BTK inhibitor designed for treatment of adult humans (column 25, lines 25-45).
As per claim 5, Acerta discloses the method of claim 3, and in a separate embodiment Acerta further discloses wherein the MALDI matrix further comprises a solvent (compound of Formula 1 was mixed with succinic acid, characteristic Raman peaks for the acetone solvate of the succinic acid co-crystal of Formula 1 were observed, where acetone is the solvent, as disclosed in claim 6 of the instant application; column 113, lines 25-45; column 114, lines 35-40).
It would have been obvious to a person of ordinary skill in the art, at the time of the invention, to have modified the method, as previously disclosed by Acerta, in order to have provided for wherein the MALDI matrix further comprises a solvent, as previously disclosed by Acerta in a separate embodiment (column 113, lines 25-45; column 114, lines 35-40), for providing the compound in the form of mixed succinic acid salt and gentisic acid salt to improve solubility and oral bioavailability of the
compound as BTK inhibitor designed for treatment of adult humans (column 25, lines 25-45).
As per claim 6, Acerta discloses the method of claim 5, and in a separate embodiment Acerta further discloses wherein the solvent is
acetone (compound of Formula 1 was mixed with succinic acid, characteristic Raman peaks for the acetone solvate of the succinic acid co-crystal of Formula 1 were observed; column 113, lines 25-45; column 114, lines 35-40).
It would have been obvious to a person of ordinary skill in the art, at the time of the invention, to have modified the method, as previously disclosed by Acerta, in order to have provided for wherein the solvent is acetone, as previously disclosed by Acerta in a separate embodiment (column 113, lines 25-45; column 114, lines 35-40), for providing the compound in the form of mixed succinic acid salt and gentisic acid salt to improve solubility and oral bioavailability of the compound as BTK inhibitor designed for treatment of adult humans (column 25, lines 25-45).
As per claim 7, Acerta discloses the method of claim 3, and Acerta further discloses wherein the MALDI matrix further comprises a counter ion or acid additive (crystalline gentisate salt was produced by mixing free base of Formula I and gentisic acid, i.e., the acid additive; column 18, lines 1-10; column 104, lines 40-67).
As per claim 8, Acerta discloses the method of claim 7, and in a separate embodiment Acerta further discloses wherein the acid additive is
H2SO4 (Form A sample was produced as a sulfate salt of Formula I; column 7, lines 35-40; column 19, lines 25-35).
It would have been obvious to a person of ordinary skill in the art, at the time of the invention, to have modified the method, as previously disclosed by Acerta,
in order to have provided for wherein the acid additive is H2SO4, as previously disclosed by Acerta in a separate embodiment (column 7, lines 35-40; column 19, lines 25-35), for providing the compound comprising imidazo [1,5-a] pyrazinyl base in the form of the sulfate salt to improve solubility and oral bioavailability of the compound as BTK inhibitor designed for treatment of adult humans (column 25, lines 25-45).
As per claim 9, Acerta discloses the method of claim 1 wherein the depositing of the one or more aromatic additives onto the sample is accomplished by manual spraying, manual dry sieve deposition, robotic spraying, sublimation, automatic spot printing, or combinations thereof (col.23, lines 39-45) (col.25, lines 52-58).
As per claim 10, Acerta discloses the method further comprising at least one of: high-resolution Raman mapping (col. 20, lines 15-20, 52-58).
As per claim 13, Acerta discloses the method wherein the sample is snap frozen or heat treated (col. 48, lines 40-45) (col. 51, lines 38-45).
As per claim 14, Acerta discloses the method further comprising embedding the sample in an embedding medium, matrix, or resin (col. 76, lines 23-26).
As per claim 18, Acerta discloses the method further comprising chemical derivatization of the sample (col. 28, Lines 25-30).
As per claim 20, Acerta discloses the method comprising analyzing one or more tryptic peptides (col. 28, lines 25-30).
As per claim 21, Acerta discloses the method comprising analyzing one or more N-glycans, peptides, lipids, metabolites, drug molecules, and drug metabolites in a spatially resolved manner (col. 28, lines 25-30).
As per claim 22, Acerta discloses the method wherein the sample is selected from an organ, a tissue, a cell, bacteria, fungi, a plant, a fruit, another lifeform, and an inanimate object (col. 41, lines 20-25)(col.9, lines 3-5).
As per claim 23, Acerta discloses the method wherein a Raman signal of the sample with the one or more aromatic compounds deposited thereon is greater than a Raman signal of the sample without the one or more aromatic compounds deposited thereon (col. 20, lines 15-20, 52-58).
Claim(s) 16-17, 19 is/are rejected under 35 U.S.C. 103 as being unpatentable over Acerta in view of Van Donselaar et al. (US 20130316365 A1) (herein after Van Donselaar).
As per claim(s) 16-17, 19, Acerta discloses all the features of the claimed invention except the limitation such as: “the method further comprising cryo-sectioning the sample.
the method of claim 16, wherein the sample is cryo-sectioned onto an indium tin oxide (ITO)-coated slide gold slides, aluminum oxide slides, or steel plates.
The method comprising analyzing one or more intact proteins”.
However, Van Donselaar from the same field of endeavor discloses a method of comprising cryo-sectioning a sample [¶0066];
the sample is cryo-sectioned onto an indium tin oxide (ITO)-coated slide gold slides, aluminum oxide slides, or steel plates [¶0034, 0086];
the method comprising analyzing one or more intact proteins [¶0079].
Therefore, it would have been obvious to a person having ordinary skill in the art before the effective filing date of the invention was made to modify the device/method/system of Acerta such that cryo-sectioning the sample; the sample is cryo-sectioned onto the indium tin oxide (ITO)-coated slide gold slides, aluminum oxide slides, or steel plates; analyzing the one or more intact proteins; as taught by Van Donselaar, for the advantages such as: to minimize contamination of the test objects.
Conclusion
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MD M. RAHMAN
Primary Patent Examiner
Art Unit 2886
/MD M RAHMAN/ Primary Examiner, Art Unit 2877
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