zx
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 1-9, 13, 14 and 17-21 are pending in the instant invention. According to the Listing of Claims, filed June 14, 2023, claims 3, 4, 6-9 were amended, claims 10-12, 15 and 16 were cancelled and claims 19-21 were added.
Status of Priority
This invention is a 35 U.S.C. § 371 National Stage Filing of International Application No. PCT/EP2021/084448, filed December 6, 2021, which claims priority under 35 U.S.C. § 119(a-d) to: a) GB 2109583.1, filed July 2, 2021; and b) GB 2019702.6, filed December 14, 2020.
Restrictions / Election of Species
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The inventor’s or joint inventor’s provisional election of the following, without traverse, in the reply filed on November 24, 2025, is acknowledged: a) Group I - claims 1-9, 13, 14 and 19-21; and b) substituted imidazo[1,2-b]pyridazine of formula (I) - p. 121, Example 17, shown to the right below, and hereafter referred to as (S)-4-cyclopropyl-N-((4,4-difluorocyclohexyl)(7-(4-((1,1-difluoroethyl)carbamoyl)tetrahydro-2H-pyran-4-yl)imidazo[1,2-b]pyridazin-2-yl)methyl)-1,2,5-oxadiazole-3-carboxamide, where A is formula (Ac), shown to the left, wherein R3 = -NR3aR3b, where R3a = -H and R3b = -CF2CH3, and R4a and R4b, together with the carbon atom to which they are attached, form tetrahydropyran-4-ylene; R1a = -H; R1b = -H; E is formula (Ea), shown to the right below; and R6 = -4-cyclopropyl-1,2,5-oxadiazol-3-yl. Claims 1-5, 9, 13 and 19-21 read on the elected
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species. Affirmation of this election must be made by the inventor or joint inventor in replying to this Office action.
Similarly, the inventor or joint inventor should further note that the requirement is still deemed proper and is therefore made FINAL.
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Likewise, the inventor or joint inventor should further note that the elected species, shown to the right below, was found to be free of the prior art. Thus, the examiner has expanded the forthcoming prosecution to include all claims relevant to the genus of Group I, for a first Office action and prosecution on the merits.
Moreover, the inventor or joint inventor should further note that claims 17 and 18 were withdrawn from further consideration, pursuant to 37 CFR 1.142(b), as being drawn to a nonelected or cancelled invention, there being no allowable generic or linking claim.
Thus, a first Office action and prosecution on the merits of claims 1-9, 13, 14 and 19-21 is contained within.
Specification Objection - Disclosure
The following guidelines illustrate the preferred layout for the specification of a utility application. These guidelines are suggested for the inventor’s or joint inventor’s use.
Arrangement of the Specification
As provided in 37 CFR 1.77(b), the specification of a utility invention should include the following sections in order. Each of the lettered items should appear in upper case, without underlining or bold type, as a section heading. If no text follows the section heading, the phrase Not Applicable should follow the section heading:
(a) TITLE OF THE INVENTION.
(b) CROSS-REFERENCE TO RELATED APPLICATIONS.
(c) STATEMENT REGARDING FEDERALLY SPONSORED RESEARCH OR
DEVELOPMENT.
(d) THE NAMES OF THE PARTIES TO A JOINT RESEARCH AGREEMENT.
(e) INCORPORATION-BY-REFERENCE OF MATERIAL SUBMITTED ON A
COMPACT DISC.
(f) BACKGROUND OF THE INVENTION.
(1) Field of the Invention.
(2) Description of Related Art (including information disclosed under 37 CFR 1.97
and 1.98).
(g) BRIEF SUMMARY OF THE INVENTION.
(h) BRIEF DESCRIPTION OF THE SEVERAL VIEWS OF THE DRAWING(S).
(i) DETAILED DESCRIPTION OF THE INVENTION.
(j) CLAIM OR CLAIMS (commencing on a separate sheet).
(k) ABSTRACT OF THE DISCLOSURE (commencing on a separate sheet).
(l) SEQUENCE LISTING (See MPEP § 2424 and 37 CFR 1.821-1.825).
The inventor or joint inventor is advised to format the specification according to 37 CFR 1.77(b) above and 37 CFR 1.77(c). Revisions should particularly include and/or address: a) section headings (b-i), where applicable; and b) bold-type, underline, and/or upper case formatting. Appropriate correction may be 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 exemplify any members or formulae illustrative of its class. Correction is required. See MPEP § 608.01(b).
The examiner suggests incorporating the structure of formula (I) into the abstract, to overcome this objection.
Claim Objections
Claim 1 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 compound of formula (I):
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(I)
or a pharmaceutically acceptable salt, stereoisomer, or tautomer thereof,
wherein:
R1a represents H, F, Cl, CH3, CHF2, or CF3;
R1b represents H, F, Cl, CH3, CHF2, or CF3;
A represents formula (Aa), formula (Ab), formula (Ac), formula (Ad), or formula (Ae):
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(Aa),
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(Ab),
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(Ac),
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(Ad), or
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(Ae),
wherein:
R2 represents OR2a, C3-9 cycloalkyl, C4-12 bicycloalkyl, C3-7 heterocycloalkyl, or C4-9 heterobicycloalkyl, wherein the C3-9 cycloalkyl, C4-12 bicycloalkyl, C3-7 heterocycloalkyl, or C4-9 heterobicycloalkyl is optionally substituted by one or more independently selected halogen substituents;
R2a represents C1-6 alkyl or C3-9 cycloalkyl;
wherein the C1-6 alkyl is optionally substituted by one or more substituents independently selected from the group consisting of halogen, CN, NO2, C(O)H, C(O)C2-6 alkyl, C(O)NH2, C(O)NHC1-6 alkyl, C(O)N(C1-6 alkyl)2, C(O)OH, C(O)OC2-6 alkyl, NH2, NHC1-6 alkyl, NHC(O)C2-6 alkyl, NHC(O)OC2-6 alkyl, NHS(O)2C1-6 alkyl, N(C1-6 alkyl)2, OH, OC1-6 alkyl, OCHF2, OCF3, =O, SC1-6 alkyl, S(O)C1-6 alkyl, S(NC1-6 alkyl)(O)C1-6 alkyl, S(O)2C1-6 alkyl, S(O)2NH2, S(O)2NHC1-6 alkyl, and S(O)2N(C1-6 alkyl)2; and
wherein the C3-9 cycloalkyl is optionally substituted by one or more substituents independently selected from the group consisting of halogen, CN, NO2, C1-6 alkyl, CF3, C(O)H, C(O)C2-6 alkyl, C(O)NH2, C(O)NHC1-6 alkyl, C(O)N(C1-6 alkyl)2, C(O)OH, C(O)OC2-6 alkyl, NH2, NHC1-6 alkyl, NHC(O)C2-6 alkyl, NHC(O)OC2-6 alkyl, NHS(O)2C1-6 alkyl, N(C1-6 alkyl)2, OH, OC1-6 alkyl, OCHF2, OCF3, =O, SC1-6 alkyl, S(O)C1-6 alkyl, S(NC1-6 alkyl)(O)C1-6 alkyl, S(O)2C1-6 alkyl, S(O)2NH2, S(O)2NHC1-6 alkyl, and S(O)2N(C1-6 alkyl)2;
R3 represents NR3aR3b or formula (Wa):
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(Wa);
R3a represents H or C1-6 alkyl;
R3b represents C1-6 alkyl, C1-6 alkylene-C3-7 cycloalkyl, C1-6 alkylene-C3-7 heterocycloalkyl, C1-6 alkylene-aryl, C1-6 alkylene-heteroaryl, C3-7 cycloalkyl, C4-12 bicycloalkyl, C3-7 heterocycloalkyl, aryl, or heteroaryl;
wherein any C1-6 alkyl or C1-6 alkylene is optionally substituted by one or more substituents independently selected from the group consisting of halogen, CN, NO2, C(O)H, C(O)C2-6 alkyl, C(O)NH2, C(O)NHC1-6 alkyl, C(O)N(C1-6 alkyl)2, C(O)OH, C(O)OC2-6 alkyl, NH2, NHC1-6 alkyl, NHC(O)C2-6 alkyl, NHC(O)OC2-6 alkyl, NHS(O)2C1-6 alkyl, N(C1-6 alkyl)2, OH, OC1-6 alkyl, OCHF2, OCF3, OCF2CH3, OCHFCH2F, OCH2CHF2, OCHFCHF2, OCF2CH2F, OCH2CF3, SC1-6 alkyl, S(O)C1-6 alkyl, S(NC1-6 alkyl)(O)C1-6 alkyl, S(O)2C1-6 alkyl, S(O)2NH2, S(O)2NHC1-6 alkyl, and S(O)2N(C1-6 alkyl)2; and
wherein any C3-7 cycloalkyl, C4-12 bicycloalkyl, C3-7 heterocycloalkyl, aryl, or heteroaryl is optionally substituted by one or more substituents independently selected from the group consisting of halogen, CN, NO2, C1-6 alkyl, C(O)H, C(O)C2-6 alkyl, C(O)NH2, C(O)NHC1-6 alkyl, C(O)N(C1-6 alkyl)2, C(O)OH, C(O)OC2-6 alkyl, NH2, NHC1-6 alkyl, NHC(O)C2-6 alkyl, NHC(O)OC2-6 alkyl, NHS(O)2C1-6 alkyl, N(C1-6 alkyl)2, OH, OC1-6 alkyl, OCHF2, OCF3, OCF2CH3, OCHFCH2F, OCH2CHF2, OCHFCHF2, OCF2CH2F, OCH2CF3, =O, SC1-6 alkyl, S(O)C1-6 alkyl, S(NC1-6 alkyl)(O)C1-6 alkyl, S(O)2C1-6 alkyl, S(O)2NH2, S(O)2NHC1-6 alkyl, and S(O)2N(C1-6 alkyl)2;
(i) W represents the residue of a saturated monocyclic ring;
wherein the monocyclic ring contains 3, 4, 5, or 6 C atoms, 1 N heteroatom, and optionally 1, 2, or 3 additional heteroatoms or heteroatomic groups independently selected from the group consisting of N, NH, O, and S;
wherein the monocyclic ring contains no more than 1 O heteroatom or 1 S heteroatom; and
wherein the monocyclic ring is optionally substituted by one or more substituents independently selected from the group consisting of halogen, CN, C1-6 alkyl, CF3, C1-6 alkyl-C(O)OH, C1-6 alkyl-C(O)OC2-6 alkyl, C1-6 aminoalkyl, C1-6 alkyl-N(C1-6 alkyl)2, C1-6 hydroxyalkyl, C1-6 alkyl-OC1-6 alkyl, C(O)H, C(O)C2-6 alkyl, C(O)NH2, C(O)NHC1-6 alkyl, C(O)N(C1-6 alkyl)2, C(O)OH, C(O)OC2-6 alkyl, NH2, NHC1-6 alkyl, NHC(O)C2-6 alkyl, NHC(O)OC2-6 alkyl, NHS(O)2C1-6 alkyl, N(C1-6 alkyl)2, OH, OC1-6 alkyl, OCHF2, OCF3, =O, SC1-6 alkyl, and S(O)2C1-6 alkyl;
(ii) W represents the residue of a saturated bicyclic ring system;
wherein the bicyclic ring system contains 4, 5, 6, 7, 8, 9, or 10 C atoms, 1 N heteroatom, and optionally 1, 2, or 3 additional heteroatoms or heteroatomic groups independently selected from the group consisting of N, NH, O, and S;
wherein the bicyclic ring system contains no more than 1 O heteroatom or 1 S heteroatom; and
wherein the bicyclic ring system is optionally substituted by one or more substituents independently selected from the group consisting of halogen, CN, C1-6 alkyl, CF3, C1-6 alkyl-C(O)OH, C1-6 alkyl-C(O)OC2-6 alkyl, C1-6 aminoalkyl, C1-6 alkyl-N(C1-6 alkyl)2, C1-6 hydroxyalkyl, C1-6 alkyl-OC1-6 alkyl, C(O)H, C(O)C2-6 alkyl, C(O)NH2, C(O)NHC1-6 alkyl, C(O)N(C1-6 alkyl)2, C(O)OH, C(O)OC2-6 alkyl, NH2, NHC1-6 alkyl, NHC(O)C2-6 alkyl, NHC(O)OC2-6 alkyl, NHS(O)2C1-6 alkyl, N(C1-6 alkyl)2, OH, OC1-6 alkyl, OCHF2, OCF3, =O, SC1-6 alkyl, and S(O)2C1-6 alkyl;
(iii) W represents the residue of a saturated spirocyclic ring system;
wherein the spirocyclic ring system contains 5, 6, 7, 8, 9, or 10 C atoms, 1 N heteroatom, and optionally 1, 2, or 3 additional heteroatoms or heteroatomic groups independently selected from the group consisting of N, NH, O, and S;
wherein the spirocyclic ring system contains no more than 1 O heteroatom or 1 S heteroatom; and
wherein the spirocyclic ring system is optionally substituted by one or more substituents independently selected from the group consisting of halogen, CN, C1-6 alkyl, CF3, C1-6 alkyl-C(O)OH, C1-6 alkyl-C(O)OC2-6 alkyl, C1-6 aminoalkyl, C1-6 alkyl-N(C1-6 alkyl)2, C1-6 hydroxyalkyl, C1-6 alkyl-OC1-6 alkyl, C(O)H, C(O)C2-6 alkyl, C(O)NH2, C(O)NHC1-6 alkyl, C(O)N(C1-6 alkyl)2, C(O)OH, C(O)OC2-6 alkyl, NH2, NHC1-6 alkyl, NHC(O)C2-6 alkyl, NHC(O)OC2-6 alkyl, NHS(O)2C1-6 alkyl, N(C1-6 alkyl)2, OH, OC1-6 alkyl, OCHF2, OCF3, =O, SC1-6 alkyl, and S(O)2C1-6 alkyl; and
the asterisk (*) represents the point of attachment to the remainder of the molecule;
R4a represents H, F, C1-6 alkyl, or OH, wherein the C1-6 alkyl is optionally substituted by one or more independently selected from the group consisting of halogen, CN, NO2, C(O)H, C(O)C2-6 alkyl, C(O)NH2, C(O)NHC1-6 alkyl, C(O)N(C1-6 alkyl)2, C(O)OH, C(O)OC2-6 alkyl, NH2, NHC1-6 alkyl, NHC(O)C2-6 alkyl, NHC(O)OC2-6 alkyl, NHS(O)2C1-6 alkyl, N(C1-6 alkyl)2, OH, OC1-6 alkyl, OCHF2, OCF3, OCF2CH3, OCHFCH2F, OCH2CHF2, OCHFCHF2, OCF2CH2F, OCH2CF3, SC1-6 alkyl, S(O)C1-6 alkyl, S(NC1-6 alkyl)(O)C1-6 alkyl, S(O)2C1-6 alkyl, S(O)2NH2, S(O)2NHC1-6 alkyl, and S(O)2N(C1-6 alkyl)2;
R4b represents H, F, C1-6 alkyl, or OH, wherein the C1-6 alkyl is optionally substituted by one or more independently selected from the group consisting of halogen, CN, NO2, C(O)H, C(O)C2-6 alkyl, C(O)NH2, C(O)NHC1-6 alkyl, C(O)N(C1-6 alkyl)2, C(O)OH, C(O)OC2-6 alkyl, NH2, NHC1-6 alkyl, NHC(O)C2-6 alkyl, NHC(O)OC2-6 alkyl, NHS(O)2C1-6 alkyl, N(C1-6 alkyl)2, OH, OC1-6 alkyl, OCHF2, OCF3, OCF2CH3, OCHFCH2F, OCH2CHF2, OCHFCHF2, OCF2CH2F, OCH2CF3, SC1-6 alkyl, S(O)C1-6 alkyl, S(NC1-6 alkyl)(O)C1-6 alkyl, S(O)2C1-6 alkyl, S(O)2NH2, S(O)2NHC1-6 alkyl, and S(O)2N(C1-6 alkyl)2; or
R4a and R4b, taken together with the carbon atom to which they are both attached, represent a C3-9 cycloalkylene or C3-7 heterocycloalkylene, wherein the C3-9 cycloalkylene or C3-7 heterocycloalkylene is optionally substituted by one or more substituents independently selecte from the group consisting of halogen, CN, NO2, C1-6 alkyl, CF3, C1-6 aminoalkyl, C1-6 alkyl-NHC(O)C2-6 alkyl, C1-6 hydroxyalkyl, C(O)H, C(O)C2-6 alkyl, C(O)NH2, C(O)NHC1-6 alkyl, C(O)N(C1-6 alkyl)2, C(O)OH, C(O)OC2-6 alkyl, NH2, NHC1-6 alkyl, NHC(O)C2-6 alkyl, NHC(O)OC2-6 alkyl, NHS(O)2C1-6 alkyl, N(C1-6 alkyl)2, OH, OC1-6 alkyl, OCHF2, OCF3, OCF2CH3, OCHFCH2F, OCH2CHF2, OCHFCHF2, OCF2CH2F, OCH2CF3, =O, SC1-6 alkyl, S(O)C1-6 alkyl, S(NC1-6 alkyl)(O)C1-6 alkyl, S(O)2C1-6 alkyl, S(O)2NH2, S(O)2NHC1-6 alkyl, S(O)2N(C1-6 alkyl)2, cyclopropyl, pyrrolidinyl, tetrahydropyranyl, piperazinyl, morpholinyl, phenyl, and fluorophenyl;
Y represents -CR5aR5b-, -NR7-, -O-, -S-, -S(O)-, -S(NR8)(O)-, or -S(O)2-;
R5a represents H, F, CH3, CHF2, or CF3;
R5b represents H, F, CH3, or OH; or
R5a and R5b, taken together with the carbon atom to which they are both attached, represent cyclopropylene;
R7 represents H, C1-6 alkyl, C(O)R7a, C(O)OR7a, S(O)2R7b, C3-9 cycloalkyl, or C3-7 heterocycloalkyl, wherein the C1-6 alkyl, C3-9 cycloalkyl, or C3-7 heterocycloalkyl is optionally substituted by one or more F substituents;
R7a represents C1-6 alkyl, wherein the C1-6 alkyl is optionally substituted by one or more F substituents;
R7b represents C1-6 alkyl;
R8 represents C1-6 alkyl;
Z represents heteroaryl, wherein the heteroaryl is optionally substituted by one or more substituents independently selected from the group consisting of halogen, CN, NO2, C1-6 alkyl, CHF2, CF2CH3, CHFCH2F, CH2CHF2, C1-6 trifluoroalkyl, CH2-cyclopropyl, CH2-difluorocyclopropyl, C1-6 aminoalkyl, C1-6 (dialkylamino)alkyl, C1-6 hydroxyalkyl, C(O)H, C(O)C2-6 alkyl, C(O)NH2, C(O)NHC1-6 alkyl, C(O)N(C1-6 alkyl)2, C(O)OH, C(O)OC2-6 alkyl, NH2, NHC1-6 alkyl, NHC(O)C2-6 alkyl, NHC(O)OC2-6 alkyl, NHS(O)2C1-6 alkyl, N(C1-6 alkyl)2, OH, OC1-6 alkyl, OCHF2, OCF3, OCF2CH3, OCHFCH2F, OCH2CHF2, OCHFCHF2, OCF2CH2F, OCH2CF3, -OCH2O-, -OCF2O-, =O, O(phenyl), SC1-6 alkyl, S(O)C1-6 alkyl, S(NC1-6 alkyl)(O)C1-6 alkyl, S(O)2C1-6 alkyl, S(O)2NH2, S(O)2NHC1-6 alkyl, and S(O)2N(C1-6 alkyl)2, cyclopropyl, difluorocyclopropyl, difluorocyclobutyl, fluorobicyclo[1.1.1]pentanyl, cyanobicyclo[1.1.1]pentanyl, spiro[2.2]pentanyl, and methylspiro[2.2]pentanyl; and
the asterisk (*) represents the point of attachment to the remainder of the molecule;
E represents formula (Ea), formula (Eb), formula (Ec), formula (Ed), or formula (Ee):
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(Ea),
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(Eb),
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(Ec),
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(Ed), or
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(Ee),
wherein the asterisk (*) represents the point of attachment to the remainder of the molecule;
R6 represents C1-6 alkyl, C1-6 alkylene-C3-9 cycloalkyl, C1-6 alkylene-C3-7 heterocycloalkyl, C1-6 alkylene-aryl, C1-6 alkylene-heteroaryl, NR6bR6c, OR6a, C3-9 cycloalkyl, C3-7 heterocycloalkyl, aryl, or heteroaryl, wherein the C1-6 alkyl, C1-6 alkylene-C3-9 cycloalkyl, C1-6 alkylene-C3-7 heterocycloalkyl, C1-6 alkylene-aryl, C1-6 alkylene-heteroaryl, C3-9 cycloalkyl, C3-7 heterocycloalkyl, aryl, or heteroaryl is optionally substituted by one or more substituents independently selected from the group consisting of halogen, CN, NO2, C1-6 alkyl, CF3, C1-6 aminoalkyl, C1-6 alkyl-NHC(O)C2-6 alkyl, C1-6 hydroxyalkyl, C(O)H, C(O)C2-6 alkyl, C(O)NH2, C(O)NHC1-6 alkyl, C(O)N(C1-6 alkyl)2, C(O)OH, C(O)OC2-6 alkyl, NH2, NHC1-6 alkyl, NHC(O)C2-6 alkyl, NHC(O)OC2-6 alkyl, NHS(O)2C1-6 alkyl, N(C1-6 alkyl)2, OH, OC1-6 alkyl, OCHF2, OCF3, =O, SC1-6 alkyl, S(O)C1-6 alkyl, S(NC1-6 alkyl)(O)C1-6 alkyl, S(O)2C1-6 alkyl, S(O)2NH2, S(O)2NHC1-6 alkyl, S(O)2N(C1-6 alkyl)2, cyclopropyl, pyrrolidinyl, tetrahydropyranyl, piperazinyl, morpholinyl, phenyl, and fluorophenyl;
R6a represents C1-6 alkyl, C3-9 cycloalkyl, or C3-7 heterocycloalkyl;
wherein the C1-6 alkyl is optionally substituted by one or more substituents independently selected from the group consisting of halogen, CN, NO2, C(O)H, C(O)C2-6 alkyl, C(O)NH2, C(O)NHC1-6 alkyl, C(O)N(C1-6 alkyl)2, C(O)OH, C(O)OC2-6 alkyl, NH2, NHC1-6 alkyl, NHC(O)C2-6 alkyl, NHC(O)OC2-6 alkyl, NHS(O)2C1-6 alkyl, N(C1-6 alkyl)2, OH, OC1-6 alkyl, OCHF2, OCF3, SC1-6 alkyl, S(O)C1-6 alkyl, S(O)2C1-6 alkyl, S(O)2NH2, S(O)2NHC1-6 alkyl, and S(O)2N(C1-6 alkyl)2; and
wherein the C3-9 cycloalkyl or C3-7 heterocycloalkyl is optionally substituted by one or more substituents independently selected from the group consisting of halogen, CN, NO2, C1-6 alkyl, CF3, C1-6 aminoalkyl, C1-6 hydroxyalkyl, C(O)H, C(O)C2-6 alkyl, C(O)NH2, C(O)NHC1-6 alkyl, C(O)N(C1-6 alkyl)2, C(O)OH, C(O)OC2-6 alkyl, NH2, NHC1-6 alkyl, NHC(O)C2-6 alkyl, NHC(O)OC2-6 alkyl, NHS(O)2C1-6 alkyl, N(C1-6 alkyl)2, OH, OC1-6 alkyl, OCHF2, OCF3, =O, SC1-6 alkyl, S(O)C1-6 alkyl, S(O)2C1-6 alkyl, S(O)2NH2, S(O)2NHC1-6 alkyl, and S(O)2N(C1-6 alkyl)2;
R6b represents H or C1-6 alkyl; and
R6c represents H or C1-6 alkyl; or
R6b and R6c, taken together with the nitrogen atom to which they are both attached, represent azetidin-1-yl, pyrrolidin-1-yl, piperidin-1-yl, homopiperidin-1-yl, isoxazolidin-2-yl, oxazolidin-3-yl, isothiazolidin-2-yl, thiazolidin-3-yl, piperazin-1-yl, morpholin-4-yl, thiomorpholin-4-yl, homopiperazin-1-yl, or homomorpholin-4-yl, wherein the azetidin-1-yl, pyrrolidin-1-yl, piperidin-1-yl, homopiperidin-1-yl, isoxazolidin-2-yl, oxazolidin-3-yl, isothiazolidin-2-yl, thiazolidin-3-yl, piperazin-1-yl, morpholin-4-yl, thiomorpholin-4-yl, homopiperazin-1-yl, or homomorpholin-4-yl is optionally substituted by one or more substituents independently selected from the group consisting of CN, C1-6 alkyl, C1-6 aminoalkyl, C1-6 alkyl-NHC(O)C2-6 alkyl, C1-6 hydroxyalkyl, C(O)C2-6 alkyl, C(O)NH2, C(O)OH, C(O)OC2-6 alkyl, NH2, NHC(O)C2-6 alkyl, NHC(O)OC2-6 alkyl, NHS(O)2C1-6 alkyl, OH, =O, and S(O)2C1-6 alkyl.
Appropriate correction is required. See MPEP § 2173.02.
Claim 2 is objected to because of the following informalities: for clarity and precision, the existing recitation should be replaced with the following recitation:
The compound as claimed in claim 1, or a pharmaceutically acceptable salt, stereoisomer, or tautomer thereof, wherein E represents formula (Ea) or formula (Ed):
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(Ea) or
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(Ed).
Appropriate correction is required. See MPEP § 2173.02.
Claim 3 is objected to because of the following informalities: for clarity and precision, the existing recitation should be replaced with the following recitation:
The compound as claimed in claim 1, or a pharmaceutically acceptable salt, stereoisomer, or tautomer thereof, wherein A represents formula (Aa), formula (Ac), formula (Ad), or formula (Ae):
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(Aa),
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(Ac),
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(Ad), or
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(Ae).
Appropriate correction is required. See MPEP § 2173.02.
Claim 4 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 compound as claimed in claim 1, or a pharmaceutically acceptable salt, stereoisomer, or tautomer thereof, wherein R6 represents heteroaryl, wherein the heteroaryl is optionally substituted by one or more substituents independently selected from the group consisting of halogen, CN, NO2, C1-6 alkyl, CF3, C1-6 aminoalkyl, C1-6 alkyl-NHC(O)C2-6 alkyl, C1-6 hydroxyalkyl, C(O)H, C(O)C2-6 alkyl, C(O)NH2, C(O)NHC1-6 alkyl, C(O)N(C1-6 alkyl)2, C(O)OH, C(O)OC2-6 alkyl, NH2, NHC1-6 alkyl, NHC(O)C2-6 alkyl, NHC(O)OC2-6 alkyl, NHS(O)2C1-6 alkyl, N(C1-6 alkyl)2, OH, OC1-6 alkyl, OCHF2, OCF3, =O, SC1-6 alkyl, S(O)C1-6 alkyl, S(NC1-6 alkyl)(O)C1-6 alkyl, S(O)2C1-6 alkyl, S(O)2NH2, S(O)2NHC1-6 alkyl, S(O)2N(C1-6 alkyl)2, cyclopropyl, pyrrolidinyl, tetrahydropyranyl, piperazinyl, morpholinyl, phenyl, and fluorophenyl.
Appropriate correction is required. See MPEP § 2173.02.
Claim 5 is objected to because of the following informalities: for clarity, precision and to avoid issues under 35 U.S.C. § 112(a), 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 compound as claimed in claim 1, wherein the compound is represented by formula (IIA-1):
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(IIA-1)
or a pharmaceutically acceptable salt, stereoisomer, or tautomer thereof,
wherein:
X represents CH or N; and
R16 represents CH3, CH2CH3, CH(CH3)2, or cyclopropyl.
Appropriate correction is required. See MPEP § 2173.02.
Claim 6 is objected to because of the following informalities: for clarity, precision and to avoid issues under 35 U.S.C. § 112(a), 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 compound as claimed in claim 1, wherein the compound is represented by formula (IIA-2):
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(IIA-2)
or a pharmaceutically acceptable salt, stereoisomer, or tautomer thereof,
wherein:
X represents CH or N; and
R16 represents CH3, CH2CH3, CH(CH3)2, or cyclopropyl.
Appropriate correction is required. See MPEP § 2173.02.
Claim 7 is objected to because of the following informalities: for clarity, precision and to avoid issues under 35 U.S.C. § 112(a), 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 compound as claimed in claim 1, wherein the compound is represented by formula (IIB-1):
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(IIB-1)
or a pharmaceutically acceptable salt, stereoisomer, or tautomer thereof,
wherein:
X represents CH or N; and
R16 represents CH3, CH2CH3, CH(CH3)2, or cyclopropyl.
Appropriate correction is required. See MPEP § 2173.02.
Claim 8 is objected to because of the following informalities: for clarity, precision and to avoid issues under 35 U.S.C. § 112(a), 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 compound as claimed in claim 1, wherein the compound is represented by formula (IIB-2):
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(IIB-2)
or a pharmaceutically acceptable salt, stereoisomer, or tautomer thereof,
wherein:
X represents CH or N; and
R16 represents CH3, CH2CH3, CH(CH3)2, or cyclopropyl.
Appropriate correction is required. See MPEP § 2173.02.
Claim 9 is objected to because of the following informalities: for clarity and precision, the existing recitation should be replaced with the following recitation:
The compound as claimed in claim 1, or a stereoisomer thereof, wherein the compound, or stereoisomer thereof, is selected from the group consisting of:
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1,
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2,
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3a,
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3b,
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4a,
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4b,
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5,
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6a,
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6b,
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7,
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8,
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9,
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10a,
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10b,
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11,
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12a,
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12b,
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13,
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14,
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15,
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16, and
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17,
or a pharmaceutically acceptable salt or tautomer thereof.
Appropriate correction is required. See MPEP § 2173.02.
Claim 13 is objected to because of the following informalities: for clarity, precision and to avoid issues under 35 U.S.C. § 112(a), 35 U.S.C. § 112(b) and/or 35 U.S.C. § 112(d), the existing recitation should be replaced with the following recitation:
A pharmaceutical composition comprising a pharmaceutically acceptable carrier in association with a compound as claimed in claim 1, or a pharmaceutically acceptable salt, stereoisomer, or tautomer thereof.
Appropriate correction is required. See MPEP § 2173.02.
Claim 14 is objected to because of the following informalities: for clarity, precision and to avoid issues under 35 U.S.C. § 112(a), 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 pharmaceutical composition as claimed in claim 13, wherein the pharmaceutical composition further comprises at least one additional pharmaceutically active ingredient.
Appropriate correction is required. See MPEP § 2173.02.
Claim 19 is objected to because of the following informalities: for clarity and precision, the existing recitation should be replaced with the following recitation:
The compound as claimed in claim 2, or a pharmaceutically acceptable salt, stereoisomer, or tautomer thereof, wherein A represents formula (Aa), formula (Ac), formula (Ad), or formula (Ae):
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(Aa),
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(Ac),
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(Ad), or
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(Ae).
Appropriate correction is required. See MPEP § 2173.02.
Claim 20 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 compound as claimed in claim 2, or a pharmaceutically acceptable salt, stereoisomer, or tautomer thereof, wherein R6 represents heteroaryl, wherein the heteroaryl is optionally substituted by one or more substituents independently selected from the group consisting of halogen, CN, NO2, C1-6 alkyl, CF3, C1-6 aminoalkyl, C1-6 alkyl-NHC(O)C2-6 alkyl, C1-6 hydroxyalkyl, C(O)H, C(O)C2-6 alkyl, C(O)NH2, C(O)NHC1-6 alkyl, C(O)N(C1-6 alkyl)2, C(O)OH, C(O)OC2-6 alkyl, NH2, NHC1-6 alkyl, NHC(O)C2-6 alkyl, NHC(O)OC2-6 alkyl, NHS(O)2C1-6 alkyl, N(C1-6 alkyl)2, OH, OC1-6 alkyl, OCHF2, OCF3, =O, SC1-6 alkyl, S(O)C1-6 alkyl, S(NC1-6 alkyl)(O)C1-6 alkyl, S(O)2C1-6 alkyl, S(O)2NH2, S(O)2NHC1-6 alkyl, S(O)2N(C1-6 alkyl)2, cyclopropyl, pyrrolidinyl, tetrahydropyranyl, piperazinyl, morpholinyl, phenyl, and fluorophenyl.
Appropriate correction is required. See MPEP § 2173.02.
Claim 21 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 compound as claimed in claim 3, or a pharmaceutically acceptable salt, stereoisomer, or tautomer thereof, wherein R6 represents heteroaryl, wherein the heteroaryl is optionally substituted by one or more substituents independently selected from the group consisting of halogen, CN, NO2, C1-6 alkyl, CF3, C1-6 aminoalkyl, C1-6 alkyl-NHC(O)C2-6 alkyl, C1-6 hydroxyalkyl, C(O)H, C(O)C2-6 alkyl, C(O)NH2, C(O)NHC1-6 alkyl, C(O)N(C1-6 alkyl)2, C(O)OH, C(O)OC2-6 alkyl, NH2, NHC1-6 alkyl, NHC(O)C2-6 alkyl, NHC(O)OC2-6 alkyl, NHS(O)2C1-6 alkyl, N(C1-6 alkyl)2, OH, OC1-6 alkyl, OCHF2, OCF3, =O, SC1-6 alkyl, S(O)C1-6 alkyl, S(NC1-6 alkyl)(O)C1-6 alkyl, S(O)2C1-6 alkyl, S(O)2NH2, S(O)2NHC1-6 alkyl, S(O)2N(C1-6 alkyl)2, cyclopropyl, pyrrolidinyl, tetrahydropyranyl, piperazinyl, morpholinyl, phenyl, and fluorophenyl.
Appropriate correction is required. See MPEP § 2173.02.
Claim Rejections - 35 U.S.C. § 112(a)
The following is a quotation of the first paragraph of 35 U.S.C. § 112:
(a) IN GENERAL. The specification shall contain a written description of the invention, and of the manner and process of making and using it, in such full, clear, concise, and exact terms as to enable any person skilled in the art to which it pertains, or with which it is most nearly connected, to make and use the same, and shall set forth the best mode contemplated by the inventor or joint inventor of carrying out the invention.
N-oxides of substituted imidazo[1,2-b]pyridazines of the formula (I)
Claims 1, 5-8, 13 and 14 are rejected under 35 U.S.C. § 112(a) because the specification, while being enabling for substituted imidazo[1,2-b]pyridazines of the formula (I), does not reasonably provide enablement for N-oxides of substituted imidazo[1,2-b]pyridazines of the formula (I). The specification does not enable any person skilled in the art to which it pertains, or with which it is most nearly connected, to make and/or use the invention commensurate in scope with these claims. N-oxides of substituted imidazo[1,2-b]pyridazines of the formula (I), as recited in claims 1, 5-8 and 13, respectively, have not been adequately enabled in the specification to allow any person having ordinary skill in the art, at the time this invention was made, to make and/or use N-oxides of substituted imidazo[1,2-b]pyridazines of the formula (I).
There are many factors to be considered when determining whether there is sufficient evidence to support a determination that a disclosure does not satisfy the enablement requirement and whether any necessary experimentation is undue. These factors include, but are not limited to: (a) breadth of the claims; (b) nature of the invention; (c) state of the prior art; (d) level of one of ordinary skill in the art; (e) level of predictability in the art; (f) amount of direction provided by the inventor or joint inventor; (g) existence of working examples; and (h) quantity of experimentation needed to make or use the invention based on the content of the disclosure. {See Ex parte Forman 230 USPQ 546 (Bd. Pat. App. & Inter. 1986); and In re Wands, 8 USPQ2d 1400 (Fed. Cir. 1988)}.
The above factors, regarding the instant invention, are summarized as follows:
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(a) Breadth of the claims - the breadth of the claims includes substituted imidazo[1,2-b]-pyridazines of the formula (I), shown to the right below, as well as the myriad of potential N-oxides formulated from these substituted imidazo-[1,2-b]pyridazines of the formula (I), shown to the right, respectively;
(b) Nature of the invention - the nature of the invention is evaluation of substituted imidazo[1,2-b]pyridazines of the formula (I), shown to the right above, and/or N-oxides thereof, and the pharmacokinetic behavior of these substances as modulators of interleukin-17 (IL-17) activity;
(c) State of the prior art - Nature Reviews: Drug Discovery offers a snapshot of the state of the drug development art. Herein, drug development is stated to follow the widely accepted Ehrlich model which includes: (1) development of a broad synthetic organic chemistry program; (2) subsequent testing of compounds in an appropriate laboratory model for the disease to be treated; and (3) screening of compounds with low toxicity in prospective clinical trials (Jordan, V. C. Nature Reviews: Drug Discovery, 2, 2003, 205). Moreover, WO 22/128584 provides a synthesis of the instantly recited substituted imidazo[1,2-b]pyridazines of the formula (I) {Brace, et al. WO 22/128584, 2022};
(d) Level of one of ordinary skill in the art - the artisans synthesizing the inventor’s or joint inventor’s substituted imidazo[1,2-b]pyridazines of the formula (I), and/or N-oxides thereof, would be a collaborative team of synthetic chemists and/or health practitioners, possessing commensurate degree level and/or skill in the art, as well as several years of professional experience;
(e) Level of predictability in the art - Synthetic organic chemistry is quite unpredictable (See In re Marzocchi and Horton 169 USPQ at 367 ¶3). Similarly, it is unclear based on the combination of pages 43-70 of the instant specification, and Brace, et al. in WO 22/128584, whether the instantly recited N-oxides of substituted imidazo[1,2-b]-pyridazines of the formula (I), are enabled. Moreover, the following excerpt is taken from Dörwald, which has relevance to the synthesis of N-oxides of substituted imidazo[1,2-b]pyridazines of the formula (I) (Dörwald, F. Zaragoza. Side Reactions in Organic Synthesis: A Guide to Successful Synthesis Design, Weinheim: WILEY-VCH Verlag GmbH & Co. KGaA, 2005, Preface):
Most non-chemists would probably be horrified if they were to learn how many attempted syntheses fail, and how inefficient research chemists are. The ratio of successful to unsuccessful chemical experiments in a normal research laboratory is far below unity, and synthetic research chemists, in the same way as most scientists, spend most of their time working out what went wrong, and why.
Despite the many pitfalls lurking in organic synthesis, most organic chemistry textbooks and research articles do give the impression that organic reactions just proceed smoothly and that the total synthesis of complex natural products, for instance, is maybe a labor-intensive but otherwise undemanding task. In fact, most syntheses of structurally complex natural products are the result of several years of hard work by a team of chemists, with almost every step requiring careful optimization. The final synthesis usually looks quite different from that originally planned, because of unexpected difficulties encountered in the initially chosen synthetic sequence. Only the seasoned practitioner who has experienced for himself the many failures and frustrations which the development (sometimes even the repetition) of a synthesis usually implies will be able to appraise such work.
Chemists tend not to publish negative results, because these are, as opposed to positive results, never definite (and far too copious).
(f) Amount of direction provided by the inventor - the invention lacks direction with respect to making and/or using N-oxides of substituted imidazo[1,2-b]pyridazines of the formula (I);
(g) Existence of working examples - the inventor or joint inventor has provided sufficient guidance to make and/or use substituted imidazo[1,2-b]pyridazines of the formula (I); however, the disclosure is insufficient to allow extrapolation of the limited examples to enable the instantly recited N-oxides of substituted imidazo[1,2-b]pyridazines of the formula (I). The specification lacks working examples of N-oxides of substituted imidazo[1,2-b]pyridazines of the formula (I).
Within the specification, [A]t least one specific operative embodiment or example of the invention must be set forth. The example(s) and description should be of sufficient scope as to justify the scope of the claims. Markush claims must be provided with support in the disclosure for each member of the Markush group. Where the constitution and formula of a chemical compound is stated only as a probability or speculation, the disclosure is not sufficient to support claims identifying the compound by such composition or formula. See MPEP § 608.01(p) and MPEP § 2173.05.
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(h) Quantity of experimentation needed to make or use the invention based on the content of the disclosure - predicting whether a recited compound, and/or a(n) N-oxide thereof, is in fact one that produces a desired physiological effect at a therapeutic concentration and with useful kinetics, is filled with experimental uncertainty, and without proper guidance, would involve a substantial amount of experimentation (Jordan, V. C. Nature Reviews: Drug Discovery, 2, 2003, 205-213). Similarly, the specification, as originally filed, including any references incorporated therein, fails to provide the necessary support required by 35 U.S.C. § 112(a) to enable the instantly recited N-oxides of substituted imidazo[1,2-b]pyridazines of the formula (I). Thus, it is unclear, based on the guidance provided by the specification, whether a(n) N-oxide of a substituted imidazo[1,2-b]pyridazine of the formula (I), such as (S)-2-((4-cyclo-propyl-1,2,5-oxadiazole-3-carboxamido)(4,4-difluorocyclohexyl)methyl)-7-(4-((1,1-difluoroethyl)carbamoyl)tetrahydro-2H-pyran-4-yl)-4H-imidazo[1,2-b]pyridazine 4-oxide, shown to the left above, is either synthetically feasible or possesses utility as a modulator of interleukin-17 (IL-17) activity.
A conclusion of lack of enablement means that, based on the evidence regarding each of the above factors, the specification, at the time the invention was filed, would not have taught one skilled in the art how to make and/or use the full scope of the claimed invention without undue experimentation. {See In re Wright, 999 F.2d 1557, 1562, 27 USPQ2d 1510, 1513 (Fed. Cir. 1993)}.
The determination that undue experimentation would have been needed to make and use the claimed invention is not a single, simple factual determination. Rather, it is a conclusion reached by weighing all the above noted factual considerations. (See In re Wands, 858 F.2d at 737, 8 USPQ2d at 1404). These factual considerations are discussed comprehensively in MPEP § 2164.08 (scope or breadth of the claims), § 2164.05(a) (nature of the invention and state of the prior art), § 2164.05(b) (level of one of ordinary skill), § 2164.03 (level of predictability in the art and amount of direction provided by the inventor or joint inventor), § 2164.02 (the existence of working examples) and § 2164.06 (quantity of experimentation needed to make or use the invention based on the content of the disclosure).
Based on a preponderance of the evidence presented herein, the conclusion that the inventor or joint inventor is insufficiently enabled for making and/or using N-oxides of substituted imidazo[1,2-b]pyridazines of the formula (I), is clearly justified.
The examiner suggests amending the claims, particularly as stated in the section above entitled Claim Objections, to overcome this rejection.
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 1-8, 13, 14 and 19-21 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 phrase, optionally substituted, in claim 1, with regard to R2, R2a, R3b, R4a, R4b, R4a and R4b, R6, R6a, W, R6b and R6c, and Z, respectively, is a relative phrase which renders the claims indefinite. The phrase, optionally substituted, is not defined by the claims, 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 14, uses open language, such as include, to define the term, substituent, with respect to Z, as halogen, etc.; however, neither the specification, nor the claim, explicitly limits the invention to any specifically disclosed or recited embodiments. Consequently, the substituted imidazo[1,2-b]pyridazines of the formula (I) have been rendered indefinite by the use of the phrase, optionally substituted, with regard to R2, R2a, R3b, R4a, R4b, R4a and R4b, R6, R6a, W, R6b and R6c, and Z, respectively.
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