DETAILED ACTION
Notice of Pre-AIA or AIA Status
The inventor or joint inventor should note that the instant invention, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA .
Status of the Claims
Claims 34-55 are pending in the instant invention. According to the Amendments to the Claims, filed October 8, 2024, claims 1-33 were cancelled and claims 34-55 were added.
Status of Priority
This invention is a Divisional (DIV) of abandoned US Application No. 17/941,838, filed September 9, 2022, which is a Continuation (CON) of US Application No. 16/961,704, filed July 13, 2020 and now US 11,649,238, which is a 35 U.S.C. § 371 National Stage Filing of International Application No. PCT/EP2019/050983, filed January 15, 2019, which claims priority under 35 U.S.C. § 119(a-d) to: a) GB 1817616.4, filed October 29, 2018; and b) GB 1800734.4, filed January 17, 2018.
Restrictions / Election of Species
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The forthcoming first Office action and prosecution on the merits includes claims 34-55, drawn to a method of making a substituted pyrazolo-[1,5-a]pyrimidine of the formula (Ix’), shown to the right.
Thus, a first Office action and prosecution on the merits of claims 34-55 is contained within.
Specification Objection - Disclosure
The inventor or joint inventor is advised to format the specification according to 37 CFR 1.77(c). Revisions should particularly address bold-type, underline, and/or upper case formatting. Appropriate correction may be required.
Specification Objection - Title
The inventor or joint inventor is reminded of the proper content of the title of the invention.
The title of the invention should be brief, but technically accurate and descriptive and should contain fewer than 500 characters. See 37 CFR 1.72(a) and MPEP § 606.
The title of the invention is not technically accurate and descriptive. A new title is required that is clearly indicative of the invention to which the claims are directed. In the revised title, the examiner suggests identifying substituted pyrazolo[1,5-a]pyrimidines of the formula (Ix’).
The following title is suggested: PROCESS FOR PREPARING SUBSTITUTED PYRAZOLO[1,5-a]PYRIMIDINES.
Appropriate correction is required.
Specification Objection - Abstract
The inventor or joint inventor is reminded of the proper content of an abstract of the disclosure.
With regard particularly to chemical patents, for compounds or compositions, the general nature of the compound or composition should be given as well as the use thereof, e.g., The compounds are of the class of alkyl benzene sulfonyl ureas, useful as oral anti-diabetics. Exemplification of a species could be illustrative of members of the class. For processes, the reactions, reagents and process conditions should be stated, generally illustrated by a single example, unless variations are necessary. See MPEP § 608.01(b), Section B.
The abstract of the disclosure is objected to because it fails to the state reactions, reagents and process conditions for the method of making a substituted pyrazolo[1,5-a]pyrimidine of the formula (Ix’). Correction is required. See MPEP § 608.01(b).
The examiner suggests incorporating the reactions, reagents and process conditions for the method of making a substituted pyrazolo[1,5-a]pyrimidine of the formula (Ix’) into the abstract, to overcome this objection.
Claim Objections
Claim 34 is objected to because of the following informalities: for clarity, precision and to avoid issues under 35 U.S.C. § 112(a) and/or 35 U.S.C. § 112(b), the existing recitation should be replaced with the following recitation:
A process for preparing a compound of formula (Ix’):
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(Ix’)
wherein:
R5 is pyazol-1-yl or imidazol-2-yl;
wherein the pyrazol-1-yl is optionally substituted at the 4-position by 1 CH3 substituent and further optionally substituted at the 5-position by 1 C1-3 alkyl substituent; and
wherein the imidazol-2-yl is optionally substituted at the 1-position by 1 C1-3 alkyl substituent and further optionally substituted at the 5-position by 1 CH3 substituent;
Z is CH;
X is N;
Y is C;
W is C;
R1 is C(O)NR1aR1b, OC1-6 alkyl, S(O)R1c, S(O)2R1c, or S(O)2NR1aR1b;
R1a is C1-3 alkyl, C1-3 haloalkyl, C1-3 hydroxyalkyl, C1-3 alkyl-OC1-3 alkyl, tetrahydrofuranyl, or tetrahydropyranyl;
R1b is H or C1-3 alkyl; or
R1a and R1b, taken together with the nitrogen heteroatom to which they are attached, form a 4- to 7-membered heterocyclyl;
wherein the 4- to 7-membered heterocyclyl contains ring carbon atoms and 0 or 1 additional ring oxygen heteroatom; and
wherein the 4- to 7-membered heterocyclyl is optionally substituted by 1 or 2 substituents independently selected from the group consisting of halo, C1-3 alkyl, C1-3 hydroxyalkyl, OH, OC1-3 alkyl, and =O; or
wherein the 4- to 7-membered heterocyclyl is ortho-fused or spiro-fused to an unsubstituted 4- to 6-membered cycloalkylene or an unsubstituted, saturated 4- to 6-membered heterocyclylene;
R1c is C1-3 alkyl, C1-3 hydroxyalkyl, C1-3 alkyl-OC1-3 alkyl, OH, or OC1-3 alkyl;
R2 is H, halo, C1-3 alkyl, or OR2a;
R2a is H, CH3, CH2CH3, or CH2CH2CH3; and
R3 is H or halo;
wherein the process comprises the following step:
treating a compound of formula (VII):
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(VII)
wherein:
R5 is pyazol-1-yl or imidazol-2-yl;
wherein the pyrazol-1-yl is optionally substituted at the 4-position by 1 CH3 substituent and further optionally substituted at the 5-position by 1 C1-3 alkyl substituent; and
wherein the imidazol-2-yl is optionally substituted at the 1-position by 1 C1-3 alkyl substituent and further optionally substituted at the 5-position by 1 CH3 substituent;
Z is CH;
X is N;
Y is C; and
W is C;
with a boronic ester of the following formula:
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wherein:
R1 is C(O)NR1aR1b, OC1-6 alkyl, S(O)R1c, S(O)2R1c, or S(O)2NR1aR1b;
R1a is C1-3 alkyl, C1-3 haloalkyl, C1-3 hydroxyalkyl, C1-3 alkyl-OC1-3 alkyl, tetrahydrofuranyl, or tetrahydropyranyl;
R1b is H or C1-3 alkyl; or
R1a and R1b, taken together with the nitrogen heteroatom to which they are attached, form a 4- to 7-membered heterocyclyl;
wherein the 4- to 7-membered heterocyclyl contains ring carbon atoms and 0 or 1 additional ring oxygen heteroatom; and
wherein the 4- to 7-membered heterocyclyl is optionally substituted by 1 or 2 substituents independently selected from the group consisting of halo, C1-3 alkyl, C1-3 hydroxyalkyl, OH, OC1-3 alkyl, and =O; or
wherein the 4- to 7-membered heterocyclyl is ortho-fused or spiro-fused to an unsubstituted 4- to 6-membered cycloalkylene or an unsubstituted, saturated 4- to 6-membered heterocyclylene;
R1c is C1-3 alkyl, C1-3 hydroxyalkyl, C1-3 alkyl-OC1-3 alkyl, OH, or OC1-3 alkyl;
R2 is H, halo, C1-3 alkyl, or OR2a;
R2a is H, CH3, CH2CH3, or CH2CH2CH3; and
R3 is H or halo;
in the presence of a palladium catalyst, a solvent, and a base, to provide a compound of formula (Ix’):
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(Ix’)
wherein:
R5 is pyazol-1-yl or imidazol-2-yl;
wherein the pyrazol-1-yl is optionally substituted at the 4-position by 1 CH3 substituent and further optionally substituted at the 5-position by 1 C1-3 alkyl substituent; and
wherein the imidazol-2-yl is optionally substituted at the 1-position by 1 C1-3 alkyl substituent and further optionally substituted at the 5-position by 1 CH3 substituent;
Z is CH;
X is N;
Y is C;
W is C;
R1 is C(O)NR1aR1b, OC1-6 alkyl, S(O)R1c, S(O)2R1c, or S(O)2NR1aR1b;
R1a is C1-3 alkyl, C1-3 haloalkyl, C1-3 hydroxyalkyl, C1-3 alkyl-OC1-3 alkyl, tetrahydrofuranyl, or tetrahydropyranyl;
R1b is H or C1-3 alkyl; or
R1a and R1b, taken together with the nitrogen heteroatom to which they are attached, form a 4- to 7-membered heterocyclyl;
wherein the 4- to 7-membered heterocyclyl contains ring carbon atoms and 0 or 1 additional ring oxygen heteroatom; and
wherein the 4- to 7-membered heterocyclyl is optionally substituted by 1 or 2 substituents independently selected from the group consisting of halo, C1-3 alkyl, C1-3 hydroxyalkyl, OH, OC1-3 alkyl, and =O; or
wherein the 4- to 7-membered heterocyclyl is ortho-fused or spiro-fused to an unsubstituted 4- to 6-membered cycloalkylene or an unsubstituted, saturated 4- to 6-membered heterocyclylene;
R1c is C1-3 alkyl, C1-3 hydroxyalkyl, C1-3 alkyl-OC1-3 alkyl, OH, or OC1-3 alkyl;
R2 is H, halo, C1-3 alkyl, or OR2a;
R2a is H, CH3, CH2CH3, or CH2CH2CH3; and
R3 is H or halo.
Appropriate correction is required. See MPEP § 2173.02.
Claim 35 is objected to because of the following informalities: for clarity, precision and to avoid issues under 35 U.S.C. § 112(b) and/or 35 U.S.C. § 112(d), the existing recitation should be replaced with the following recitation:
The process of claim 34, wherein the process comprises treating a compound of formula (VII) with a boronic ester in the presence of bis(diphenylphosphino)ferrocene)palladium(II) chloride (PdCl2(dppf)), 1,4-dioxane and water, and sodium carbonate, to provide a compound of formula (Ix’).
Appropriate correction is required. See MPEP § 2173.02.
Claim 36 is objected to because of the following informalities: for clarity, precision and to avoid issues under 35 U.S.C. § 112(b) and/or 35 U.S.C. § 112(d), the existing recitation should be replaced with the following recitation:
The process of claim 34, wherein the process further comprises:
treating a compound of formula (V):
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(V)
wherein:
R5 is pyazol-1-yl or imidazol-2-yl;
wherein the pyrazol-1-yl is optionally substituted at the 4-position by 1 CH3 substituent and further optionally substituted at the 5-position by 1 C1-3 alkyl substituent; and
wherein the imidazol-2-yl is optionally substituted at the 1-position by 1 C1-3 alkyl substituent and further optionally substituted at the 5-position by 1 CH3 substituent;
Z is CH;
X is N;
Y is C; and
W is C;
with a Grignard reagent in the presence of a solvent, to provide the compound of formula (VII):
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(VII)
wherein:
R5 is pyazol-1-yl or imidazol-2-yl;
wherein the pyrazol-1-yl is optionally substituted at the 4-position by 1 CH3 substituent and further optionally substituted at the 5-position by 1 C1-3 alkyl substituent; and
wherein the imidazol-2-yl is optionally substituted at the 1-position by 1 C1-3 alkyl substituent and further optionally substituted at the 5-position by 1 CH3 substituent;
Z is CH;
X is N;
Y is C; and
W is C.
Appropriate correction is required. See MPEP § 2173.02.
Claim 37 is objected to because of the following informalities: for clarity, precision and to avoid issues under 35 U.S.C. § 112(b) and/or 35 U.S.C. § 112(d), the existing recitation should be replaced with the following recitation:
The process of claim 36, wherein the process comprises treating a compound of formula (V) with methylmagnesium bromide in the presence of dichloromethane (DCM), to provide the compound of formula (VII).
Appropriate correction is required. See MPEP § 2173.02.
Claim 38 is objected to because of the following informalities: for clarity, precision and to avoid issues under 35 U.S.C. § 112(b) and/or 35 U.S.C. § 112(d), the existing recitation should be replaced with the following recitation:
The process of claim 36, wherein the process further comprises:
treating a compound of formula (VI):
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(VI)
wherein:
L is Cl or Br;
Z is CH;
X is N;
Y is C; and
W is C;
with an amine of the following formula:
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,
wherein:
R5 is pyazol-1-yl or imidazol-2-yl;
wherein the pyrazol-1-yl is optionally substituted at the 4-position by 1 CH3 substituent and further optionally substituted at the 5-position by 1 C1-3 alkyl substituent; and
wherein the imidazol-2-yl is optionally substituted at the 1-position by 1 C1-3 alkyl substituent and further optionally substituted at the 5-position by 1 CH3 substituent;
in the presence of a base and a solvent, to provide the compound of formula (V):
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(V)
wherein:
R5 is pyazol-1-yl or imidazol-2-yl;
wherein the pyrazol-1-yl is optionally substituted at the 4-position by 1 CH3 substituent and further optionally substituted at the 5-position by 1 C1-3 alkyl substituent; and
wherein the imidazol-2-yl is optionally substituted at the 1-position by 1 C1-3 alkyl substituent and further optionally substituted at the 5-position by 1 CH3 substituent;
Z is CH;
X is N;
Y is C; and
W is C.
Appropriate correction is required. See MPEP § 2173.02.
Claim 39 is objected to because of the following informalities: for clarity, precision and to avoid issues under 35 U.S.C. § 112(b) and/or 35 U.S.C. § 112(d), the existing recitation should be replaced with the following recitation:
The process of claim 38, wherein the process comprises:
treating a compound of formula (VI) with an amine of the following formula:
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,
in the presence of a base and a solvent, to provide the compound of formula (V).
Appropriate correction is required. See MPEP § 2173.02.
Claim 40 is objected to because of the following informalities: for clarity, precision and to avoid issues under 35 U.S.C. § 112(b) and/or 35 U.S.C. § 112(d), the existing recitation should be replaced with the following recitation:
The process of claim 38, wherein the process comprises treating a compound of formula (VI) with an amine in the presence of N,.N-diisopropylethylamine (DIPEA) and a solvent, to provide the compound of formula (V).
Appropriate correction is required. See MPEP § 2173.02.
Claim 41 is objected to because of the following informalities: for clarity, precision and to avoid issues under 35 U.S.C. § 112(b) and/or 35 U.S.C. § 112(d), the existing recitation should be replaced with the following recitation(s):
41. The process of claim 38, wherein the process comprises:
treating a compound of formula (VIa):
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(VIa)
with an amine of the following formula:
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,
wherein:
R5 is pyazol-1-yl or imidazol-2-yl;
wherein the pyrazol-1-yl is optionally substituted at the 4-position by 1 CH3 substituent and further optionally substituted at the 5-position by 1 C1-3 alkyl substituent; and
wherein the imidazol-2-yl is optionally substituted at the 1-position by 1 C1-3 alkyl substituent and further optionally substituted at the 5-position by 1 CH3 substituent;
in the presence of a base and a solvent, to provide the compound of formula (V):
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(V)
wherein:
R5 is pyazol-1-yl or imidazol-2-yl;
wherein the pyrazol-1-yl is optionally substituted at the 4-position by 1 CH3 substituent and further optionally substituted at the 5-position by 1 C1-3 alkyl substituent; and
wherein the imidazol-2-yl is optionally substituted at the 1-position by 1 C1-3 alkyl substituent and further optionally substituted at the 5-position by 1 CH3 substituent.
56. The process of claim 41, wherein the process comprises the following steps:
(i) reacting a compound of formula (IX):
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(IX)
with a sodium salt of diethyl oxalacetate of the following formula:
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,
in the presence of an acid, a solvent, and heat, to provide a compound of formula (VIII):
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(VIII);
(ii) treating the compound of formula (VIII) provided in step (i) above, with a chlorinating reagent in the presence of heat, to provide a compound of formula (X):
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(X); and
(iii) treating the compound of formula (X) provided in step (ii) above, with a bromine source or an iodine source in the presence of a solvent, to provide the compound of formula (VIa):
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(VIa).
Appropriate correction is required. See MPEP § 2173.02.
Claim 42 is objected to because of the following informalities: for clarity, precision and to avoid issues under 35 U.S.C. § 112(b) and/or 35 U.S.C. § 112(d), the existing recitation should be replaced with the following recitation:
57. The process of claim 56, wherein the process comprises treating the compound of formula (VIII) provided in step (i) with POCl3 in the presence of heat, to provide the compound of formula (X).
Appropriate correction is required. See MPEP § 2173.02.
Claim 43 is objected to because of the following informalities: for clarity, precision and to avoid issues under 35 U.S.C. § 112(b) and/or 35 U.S.C. § 112(d), the existing recitation should be replaced with the following recitation:
58. The process of claim 56, wherein the process comprises treating the compound of formula (X) provided in step (ii) with N-bromosuccinimide (NBS) or N-iodosuccinimide (NIS) in the presence of a solvent, to provide the compound of formula (VIa).
Appropriate correction is required. See MPEP § 2173.02.
Claim 44 is objected to because of the following informalities: for clarity, precision and to avoid issues under 35 U.S.C. § 112(b) and/or 35 U.S.C. § 112(d), the existing recitation should be replaced with the following recitation:
The process of claim 34, wherein R1 is C(O)NR1aR1b.
Appropriate correction is required. See MPEP § 2173.02.
Claim 45 is objected to because of the following informalities: for clarity, precision and to avoid issues under 35 U.S.C. § 112(b) and/or 35 U.S.C. § 112(d), the existing recitation should be replaced with the following recitation:
The process of claim 44, wherein R1a is C1-3 hydroxyalkyl.
Appropriate correction is required. See MPEP § 2173.02.
Claim 46 is objected to because of the following informalities: for clarity, precision and to avoid issues under 35 U.S.C. § 112(b) and/or 35 U.S.C. § 112(d), the existing recitation should be replaced with the following recitation:
The process of claim 45, wherein R1a is CH2CH2OH, CH2CH2CH2OH, or CH(CH3)CH2OH.
Appropriate correction is required. See MPEP § 2173.02.
Claim 47 is objected to because of the following informalities: for clarity, precision and to avoid issues under 35 U.S.C. § 112(b) and/or 35 U.S.C. § 112(d), the existing recitation should be replaced with the following recitation:
The process of claim 44, wherein R1b is C1-3 alkyl.
Appropriate correction is required. See MPEP § 2173.02.
Claim 48 is objected to because of the following informalities: for clarity, precision and to avoid issues under 35 U.S.C. § 112(b) and/or 35 U.S.C. § 112(d), the existing recitation should be replaced with the following recitation:
The process of claim 47, wherein R1b is CH3 or CH2CH3.
Appropriate correction is required. See MPEP § 2173.02.
Claim 49 is objected to because of the following informalities: for clarity, precision and to avoid issues under 35 U.S.C. § 112(b) and/or 35 U.S.C. § 112(d), the existing recitation should be replaced with the following recitation:
The process of claim 34, wherein R2 is C1-3 alkyl.
Appropriate correction is required. See MPEP § 2173.02.
Claim 50 is objected to because of the following informalities: for clarity, precision and to avoid issues under 35 U.S.C. § 112(b) and/or 35 U.S.C. § 112(d), the existing recitation should be replaced with the following recitation:
The process of claim 34, wherein R3 is H.
Appropriate correction is required. See MPEP § 2173.02.
Claim 51 is objected to because of the following informalities: for clarity, precision and to avoid issues under 35 U.S.C. § 112(b) and/or 35 U.S.C. § 112(d), the existing recitation should be replaced with the following recitation:
The process of claim 34, wherein R5 is imidazol-2-yl, wherein the imidazol-2-yl is optionally substituted at the 1-position by 1 C1-3 alkyl substituent and further optionally substituted at the 5-position by 1 CH3 substituent.
Appropriate correction is required. See MPEP § 2173.02.
Claim 52 is objected to because of the following informalities: for clarity, precision and to avoid issues under 35 U.S.C. § 112(b) and/or 35 U.S.C. § 112(d), the existing recitation should be replaced with the following recitation:
The process of claim 51, wherein R5 is:
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.
Appropriate correction is required. See MPEP § 2173.02.
Claim 53 is objected to because of the following informalities: for clarity, precision and to avoid issues under 35 U.S.C. § 112(b) and/or 35 U.S.C. § 112(d), the existing recitation should be replaced with the following recitation:
The process of claim 34, wherein the compound of formula (Ix’) is Compound 22:
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Compound 22.
Appropriate correction is required. See MPEP § 2173.02.
Claim 54 is objected to because of the following informalities: for clarity, precision and to avoid issues under 35 U.S.C. § 112(b) and/or 35 U.S.C. § 112(d), the existing recitation should be replaced with the following recitation:
The process of claim 34, wherein the boronic ester is Intermediate 28:
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Intermediate 28.
Appropriate correction is required. See MPEP § 2173.02.
Claim 55 is objected to because of the following informalities: for clarity, precision and to avoid issues under 35 U.S.C. § 112(b) and/or 35 U.S.C. § 112(d), the existing recitation should be replaced with the following recitation:
The process of claim 54, wherein the process comprises treating a compound of formula (VII) with the boronic ester in the presence of bis(diphenylphosphino)ferrocene)palladium(II) chloride (PdCl2(dppf)), 1,4-dioxane and water, and sodium carbonate, to provide the compound of formula (Ix’).
Appropriate correction is required. See MPEP § 2173.02.
Claim Rejections - 35 U.S.C. § 112(b)
The following is a quotation of the second paragraph of 35 U.S.C. § 112:
(b) CONCLUSION. The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the inventor or joint inventor regards as the invention.
Claims 34-53 are rejected under 35 U.S.C. § 112(b) as being indefinite for failing to set forth the subject matter which the inventor or joint inventor regards as the invention.
The inventor or joint inventor should note that the term, boronic ester, in claim 34, is a relative term which renders the claim indefinite. The term, boronic ester, is not defined by the claim, the specification does not provide an adequate standard for ascertaining the requisite degree, and one of ordinary skill in the art would not be reasonably apprised of the metes and bounds of the invention. The specification, on page 22, uses open language, such as for example, to define the term, boronic ester, as N-(3-hydroxypropyl)-2-methoxy-N-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide); however, neither the specification, nor the claim, explicitly limits the invention to any specifically disclosed or recited embodiments. Consequently, the method of making a substituted pyrazolo[1,5-a]pyrimidine of the formula (Ix’) has been rendered indefinite by the use of the term, boronic ester.
Moreover, the inventor or joint inventor should further note that [C]laims which depend from indefinite claims are also indefinite. {See Ex parte Cordova, 10 USPQ 2d 1949, 1952 (PTO Bd. App. 1989)}.
The examiner suggests amending the claims, particularly as stated in the section above entitled Claim Objections, to overcome this rejection.
Claims 34 and 36-55 are rejected under 35 U.S.C. § 112(b) as being indefinite for failing to set forth the subject matter which the inventor or joint inventor regards as the invention.
The inventor or joint inventor should note that the term, catalyst, in claim 34, is a relative term which renders the claim indefinite. The term, catalyst, is not defined by the claim, the specification does not provide an adequate standard for ascertaining the requisite degree, and one of ordinary skill in the art would not be reasonably apprised of the metes and bounds of the invention. The specification, on page 22, uses open language, such as for example, to define the term, catalyst, as PdCl2(dppf); however, neither the specification, nor the claim, explicitly limits the invention to any specifically disclosed or recited embodiments. Consequently, the method of making a substituted pyrazolo[1,5-a]pyrimidine of the formula (Ix’) has been rendered indefinite by the use of the term, catalyst.
Moreover, the inventor or joint inventor should further note that [C]laims which depend from indefinite claims are also indefinite. {See Ex parte Cordova, 10 USPQ 2d 1949, 1952 (PTO Bd. App. 1989)}.
The examiner suggests amending the claims, particularly as stated in the section above entitled Claim Objections, to overcome this rejection.
Claims 38 and 40-43 are further rejected under 35 U.S.C. § 112(b) as being indefinite for failing to set forth the subject matter which the inventor or joint inventor regards as the invention.
The inventor or joint inventor should note that the term, amine, in claim 38, is a relative term which renders the claim indefinite. The term, amine, is not defined by the claim, the specification does not provide an adequate standard for ascertaining the requisite degree, and one of ordinary skill in the art would not be reasonably apprised of the metes and bounds of the invention. The specification, on page 22, uses open language, such as for example, to define the term, amine, as (3-(1-methyl-1H-imidazol-2-yl)phenyl)methylamine); however, neither the specification, nor the claim, explicitly limits the invention to any specifically disclosed or recited embodiments. Consequently, the method of making a substituted pyrazolo[1,5-a]pyrimidine of the formula (Ix’) has been rendered indefinite by the use of the term, amine.
Moreover, the inventor or joint inventor should further note that [C]laims which depend from indefinite claims are also indefinite. {See Ex parte Cordova, 10 USPQ 2d 1949, 1952 (PTO Bd. App. 1989)}.
The examiner suggests amending the claims, particularly as stated in the section above entitled Claim Objections, to overcome this rejection.
Claim 41 is further rejected under 35 U.S.C. § 112(b) as being indefinite for failing to set forth the subject matter which the inventor or joint inventor regards as the invention.
The inventor or joint inventor should note that the term, ester, in step (i), is a relative term which renders the claim indefinite. The term, ester, is not defined by the claim, the specification does not provide an adequate standard for ascertaining the requisite degree, and one of ordinary skill in the art would not be reasonably apprised of the metes and bounds of the invention. The specification, on page 23, uses open language, such as for example, to define the term, ester, as sodium salt of diethyl oxalacetate; however, neither the specification, nor the claim, explicitly limits the invention to any specifically disclosed or recited embodiments. Consequently, the method of making a substituted pyrazolo[1,5-a]pyrimidine of the formula (VIII) has been rendered indefinite by the use of the term, ester.
The examiner suggests amending the claim, particularly as stated in the section above entitled Claim Objections, to overcome this rejection.
Claims 54 and 55 are further rejected under 35 U.S.C. § 112(b) as being indefinite for failing to set forth the subject matter which the inventor or joint inventor regards as the invention.
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The inventor or joint inventor should note that claim 54 recites the limitation, The method of claim 34, wherein the boronic ester is… methyl 2-methyl-5-(4,4,5,5-tetra-methyl-1,3,2-dioxaborolan-2-yl)benzoate (Intermediate 116), shown to the right, in lines 1-3 of the claim. There is insufficient antecedent basis, in claim 34, for this limitation, with respect to the method of making a substituted pyrazolo[1,5-a]pyrimidine of the formula (IX’). According to claim 34, R1 is recited as C(O)NR1aR1b, not C(O)OCH3, with respect to the requisite intermediate boronic esters in the method of making a substituted pyrazolo[1,5-a]-pyrimidine of the formula (IX’).
Moreover, the inventor or joint inventor should further note that [C]laims which depend from indefinite claims are also indefinite. {See Ex parte Cordova, 10 USPQ 2d 1949, 1952 (PTO Bd. App. 1989)}.
The examiner suggests amending the claims, particularly as stated in the section above entitled Claim Objections, to overcome this rejection.
Allowable Subject Matter
No claims are allowed.
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to DOUGLAS M. WILLIS, whose telephone number is 571-270-5757. The examiner may normally be reached on Monday thru Thursday from 8:00-6:00 EST. The examiner is also available on alternate Fridays.
If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Mr. Jeffrey Murray, may be reached on 571-272-9023. The fax phone number for the organization where this invention or proceeding is assigned is 571-273-8300.
Information regarding the status of an invention may be obtained from Patent Center. For more information about Patent Center, see https://www.uspto.gov/patents/apply/patent-center. Should you have questions on access to Patent Center, contact the Patent Electronic Business Center (PEBC) at 866-217-9197 (toll-free) or ebc@uspto.gov.
/DOUGLAS M WILLIS/
Primary Examiner, Art Unit 1624
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