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 .
Status of Claims
Claims 14-25 are pending. Claims 24-25 are withdrawn.
Priority
Instant application 17/785,939, filed 06/16/2022 claims priority as follows:
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Receipt is acknowledged of certified copies of papers required by 37 CFR 1.55.
Election/Restrictions
In view of applicants’ amendments to the claims, the search has been extended again to a limited number of species reading on the instant claims which are anticipated by or rendered obvious by prior art. See the rejections under 35 U.S.C. 102 and 103 further below. Further, in accordance with MPEP 803.02, the scope of examination has been limited to Applicant’s elected species, the compounds recited in claims 21 and 22, and the expanded species cited herein. Subject matter falling outside of the elected and/or expanded species has not yet been examined.
Response to Amendment/Arguments
The amendment filed 09/03/2025 has been entered. Applicant has amended claims 14 and 19-21. In view of the amendment to the claims, Applicant has overcome the objections to claim 14 and 21; the rejection of claims 14-23 under 35 U.S.C. 112; the rejection of claim 20 under 35 U.S.C. 112(b); the rejection of claims 14-20 and 23 under 35 U.S.C. 102; and the rejection of claims 14, 18-20, and 23 under 35 U.S.C. 102 previously set forth in the Office action mailed 06/06/2025. Therefore, the aforementioned objections and rejections are withdrawn.
New rejections necessitated by claim amendments are presented below.
Claim Rejections - 35 USC § 102
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.
(a)(2) the claimed invention was described in a patent issued under section 151, or in an application for patent published or deemed published under section 122(b), in which the patent or application, as the case may be, names another inventor and was effectively filed before the effective filing date of the claimed invention.
Claims 14 and 18-20 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by CAS Registry Numbers 2202412-81-3, 2202327-10-2, 2202326-61-0, 2202325-49-1, 2202261-43-4, 2202261-33-2, 2202247-39-8, 2201695-48-7, 2201618-41-7, 2201427-36-1, 2201280-94-4, 2201244-29-1, 2200845-05-0, 2200395-40-8, 2199674-57-0, 2199473-73-7, 2199473-70-4, 2199420-83-0, 2199420-81-8, 2199344-75-5, 2199343-83-2, 2199342-95-3, 2199275-47-1, 2199275-45-9, 2198662-11-0, 2198369-85-4, 2198093-31-9, 2197882-55-4, 2197806-90-7, 2197806-88-3, 2197806-86-1, 2197710-87-3, 2197639-66-8, 2189434-08-8, and 2097924-20-2 (Chemical Abstracts Service: Columbus, OH; https://stn.org; accessed October 28, 2025).
The reference compounds were entered into the CAS Registry database from a chemical catalog, and were therefore available to the public prior to the earliest priority date of the instant application. See the reference compounds and the date entered (“ED”) into the Registry database below. The reference compounds anticipate instant formula (I) when n is 1; m is 0; m’ is 1; R5 is H; R6 is H; R1 is H; R2 is a cycloalkyl group; X is CH; Y is N; and R3 is alkyl, substituted by one or more groups selected from OH, alkoxy, halogen, heteroaryl, and heterocycloalkyl.
L5 ANSWER 3 OF 37 REGISTRY COPYRIGHT 2025 ACS on STN
RN 2202412-81-3 REGISTRY
ED Entered STN: 30 Mar 2018
CN 4(3H)-Pyrimidinone, 6-cyclopropyl-3-[[1-[2-hydroxy-2-(4-thiazolyl)ethyl]-4-piperidinyl]methyl]- (CA INDEX NAME)
OTHER CA INDEX NAMES:
CN 6-Cyclopropyl-3-[[1-[2-hydroxy-2-(4-thiazolyl)ethyl]-4-piperidinyl]methyl]-4(3H)-pyrimidinone
MF C18 H24 N4 O2 S
INCH InChI=1S/C18H24N4O2S/c23-17(16-10-25-12-20-16)9-21-5-3-13(4-6-21)8-22-11-19-15(7-18(22)24)14-1-2-14/h7,10-14,17,23H,1-6,8-9H2
INKY RUSUCEFGUBGEKE-UHFFFAOYSA-N
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**PROPERTY DATA AVAILABLE IN THE 'PROP' FORMAT**
L5 ANSWER 4 OF 37 REGISTRY COPYRIGHT 2025 ACS on STN
RN 2202327-10-2 REGISTRY
ED Entered STN: 30 Mar 2018
CN 4(3H)-Pyrimidinone, 6-cyclopropyl-3-[[1-[2-(1-piperidinyl)ethyl]-4-piperidinyl]methyl]- (CA INDEX NAME)
OTHER CA INDEX NAMES:
CN 6-Cyclopropyl-3-[[1-[2-(1-piperidinyl)ethyl]-4-piperidinyl]methyl]-4(3H)-pyrimidinone
MF C20 H32 N4 O
INCH InChI=1S/C20H32N4O/c25-20-14-19(18-4-5-18)21-16-24(20)15-17-6-10-23(11-7-17)13-12-22-8-2-1-3-9-22/h14,16-18H,1-13,15H2
INKY WSRBBPVWZRFJMB-UHFFFAOYSA-N
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**PROPERTY DATA AVAILABLE IN THE 'PROP' FORMAT**
L5 ANSWER 5 OF 37 REGISTRY COPYRIGHT 2025 ACS on STN
RN 2202326-61-0 REGISTRY
ED Entered STN: 30 Mar 2018
CN 4(3H)-Pyrimidinone, 6-cyclopropyl-3-[[1-[2-(1-pyrrolidinyl)ethyl]-4-piperidinyl]methyl]- (CA INDEX NAME)
OTHER CA INDEX NAMES:
CN 6-Cyclopropyl-3-[[1-[2-(1-pyrrolidinyl)ethyl]-4-piperidinyl]methyl]-4(3H)-pyrimidinone
MF C19 H30 N4 O
INCH InChI=1S/C19H30N4O/c24-19-13-18(17-3-4-17)20-15-23(19)14-16-5-9-22(10-6-16)12-11-21-7-1-2-8-21/h13,15-17H,1-12,14H2
INKY GWCHLRBJTYTRHU-UHFFFAOYSA-N
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**PROPERTY DATA AVAILABLE IN THE 'PROP' FORMAT**
L5 ANSWER 6 OF 37 REGISTRY COPYRIGHT 2025 ACS on STN
RN 2202325-49-1 REGISTRY
ED Entered STN: 30 Mar 2018
CN 4(3H)-Pyrimidinone, 6-cyclopropyl-3-[[1-[2-(2-oxo-1-pyrrolidinyl)ethyl]-4-piperidinyl]methyl]- (CA INDEX NAME)
OTHER CA INDEX NAMES:
CN 6-Cyclopropyl-3-[[1-[2-(2-oxo-1-pyrrolidinyl)ethyl]-4-piperidinyl]methyl]-4(3H)-pyrimidinone
MF C19 H28 N4 O2
INCH InChI=1S/C19H28N4O2/c24-18-2-1-7-22(18)11-10-21-8-5-15(6-9-21)13-23-14-20-17(12-19(23)25)16-3-4-16/h12,14-16H,1-11,13H2
INKY GVEWKXHXSQAPLF-UHFFFAOYSA-N
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**PROPERTY DATA AVAILABLE IN THE 'PROP' FORMAT**
L5 ANSWER 7 OF 37 REGISTRY COPYRIGHT 2025 ACS on STN
RN 2202261-43-4 REGISTRY
ED Entered STN: 30 Mar 2018
CN 4(3H)-Pyrimidinone, 6-cyclopropyl-3-[[1-[2-hydroxy-2-(5-methyl-2-furanyl)ethyl]-4-piperidinyl]methyl]- (CA INDEX NAME)
OTHER CA INDEX NAMES:
CN 6-Cyclopropyl-3-[[1-[2-hydroxy-2-(5-methyl-2-furanyl)ethyl]-4-piperidinyl]methyl]-4(3H)-pyrimidinone
MF C20 H27 N3 O3
INCH InChI=1S/C20H27N3O3/c1-14-2-5-19(26-14)18(24)12-22-8-6-15(7-9-22)11-23-13-21-17(10-20(23)25)16-3-4-16/h2,5,10,13,15-16,18,24H,3-4,6-9,11-12H2,1H3
INKY UVJMPLKDCSEJDL-UHFFFAOYSA-N
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**PROPERTY DATA AVAILABLE IN THE 'PROP' FORMAT**
L5 ANSWER 8 OF 37 REGISTRY COPYRIGHT 2025 ACS on STN
RN 2202261-33-2 REGISTRY
ED Entered STN: 30 Mar 2018
CN 4(3H)-Pyrimidinone, 6-cyclopropyl-3-[[1-[2-(1-methyl-1H-imidazol-5-yl)ethyl]-4-piperidinyl]methyl]- (CA INDEX NAME)
OTHER CA INDEX NAMES:
CN 6-Cyclopropyl-3-[[1-[2-(1-methyl-1H-imidazol-5-yl)ethyl]-4-piperidinyl]methyl]-4(3H)-pyrimidinone
MF C19 H27 N5 O
INCH InChI=1S/C19H27N5O/c1-22-13-20-11-17(22)6-9-23-7-4-15(5-8-23)12-24-14-21-18(10-19(24)25)16-2-3-16/h10-11,13-16H,2-9,12H2,1H3
INKY YISQJSMQSLNOOW-UHFFFAOYSA-N
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Supplier: Aurora Fine Chemicals
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**PROPERTY DATA AVAILABLE IN THE 'PROP' FORMAT**
L5 ANSWER 9 OF 37 REGISTRY COPYRIGHT 2025 ACS on STN
RN 2202247-39-8 REGISTRY
ED Entered STN: 30 Mar 2018
CN 4(3H)-Pyrimidinone, 6-cyclopropyl-3-[[1-[2-(2H-1,2,3-triazol-2-yl)ethyl]-4-piperidinyl]methyl]- (CA INDEX NAME)
OTHER CA INDEX NAMES:
CN 6-Cyclopropyl-3-[[1-[2-(2H-1,2,3-triazol-2-yl)ethyl]-4-piperidinyl]methyl]-4(3H)-pyrimidinone
MF C17 H24 N6 O
INCH InChI=1S/C17H24N6O/c24-17-11-16(15-1-2-15)18-13-22(17)12-14-3-7-21(8-4-14)9-10-23-19-5-6-20-23/h5-6,11,13-15H,1-4,7-10,12H2
INKY PWXABAUBDPYTEM-UHFFFAOYSA-N
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**PROPERTY DATA AVAILABLE IN THE 'PROP' FORMAT**
L5 ANSWER 10 OF 37 REGISTRY COPYRIGHT 2025 ACS on STN
RN 2201695-48-7 REGISTRY
ED Entered STN: 29 Mar 2018
CN 5H-1,4-Diazepin-5-one, 1-[2-[4-[(4-cyclopropyl-6-oxo-1(6H)-pyrimidinyl)methyl]-1-piperidinyl]ethyl]hexahydro- (CA INDEX NAME)
OTHER CA INDEX NAMES:
CN 1-[2-[4-[(4-Cyclopropyl-6-oxo-1(6H)-pyrimidinyl)methyl]-1-piperidinyl]ethyl]hexahydro-5H-1,4-diazepin-5-one
MF C20 H31 N5 O2
INCH InChI=1S/C20H31N5O2/c26-19-5-9-24(10-6-21-19)12-11-23-7-3-16(4-8-23)14-25-15-22-18(13-20(25)27)17-1-2-17/h13,15-17H,1-12,14H2,(H,21,26)
INKY AWYIQYDOQZDDCL-UHFFFAOYSA-N
SR Chemical Catalog
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234
526
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**PROPERTY DATA AVAILABLE IN THE 'PROP' FORMAT**
L5 ANSWER 11 OF 37 REGISTRY COPYRIGHT 2025 ACS on STN
RN 2201618-41-7 REGISTRY
ED Entered STN: 29 Mar 2018
CN 4(3H)-Pyrimidinone, 6-cyclopropyl-3-[[1-[2-(tetrahydro-1,4-oxazepin-4(5H)-yl)ethyl]-4-piperidinyl]methyl]- (CA INDEX NAME)
OTHER CA INDEX NAMES:
CN 6-Cyclopropyl-3-[[1-[2-(tetrahydro-1,4-oxazepin-4(5H)-yl)ethyl]-4-piperidinyl]methyl]-4(3H)-pyrimidinone
MF C20 H32 N4 O2
INCH InChI=1S/C20H32N4O2/c25-20-14-19(18-2-3-18)21-16-24(20)15-17-4-7-23(8-5-17)10-9-22-6-1-12-26-13-11-22/h14,16-18H,1-13,15H2
INKY OTNZCZPRZZLODV-UHFFFAOYSA-N
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**PROPERTY DATA AVAILABLE IN THE 'PROP' FORMAT**
L5 ANSWER 12 OF 37 REGISTRY COPYRIGHT 2025 ACS on STN
RN 2201427-36-1 REGISTRY
ED Entered STN: 29 Mar 2018
CN 2H-Azepin-2-one, 1-[2-[4-[(4-cyclopropyl-6-oxo-1(6H)-pyrimidinyl)methyl]-1-piperidinyl]ethyl]hexahydro- (CA INDEX NAME)
OTHER CA INDEX NAMES:
CN 1-[2-[4-[(4-Cyclopropyl-6-oxo-1(6H)-pyrimidinyl)methyl]-1-piperidinyl]ethyl]hexahydro-2H-azepin-2-one
MF C21 H32 N4 O2
INCH InChI=1S/C21H32N4O2/c26-20-4-2-1-3-9-24(20)13-12-23-10-7-17(8-11-23)15-25-16-22-19(14-21(25)27)18-5-6-18/h14,16-18H,1-13,15H2
INKY QQMVDWICEHGAIN-UHFFFAOYSA-N
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**PROPERTY DATA AVAILABLE IN THE 'PROP' FORMAT**
L5 ANSWER 13 OF 37 REGISTRY COPYRIGHT 2025 ACS on STN
RN 2201280-94-4 REGISTRY
ED Entered STN: 29 Mar 2018
CN 4(3H)-Pyrimidinone, 6-cyclopropyl-3-[[1-(2-methoxyethyl)-4-piperidinyl]methyl]- (CA INDEX NAME)
OTHER CA INDEX NAMES:
CN 6-Cyclopropyl-3-[[1-(2-methoxyethyl)-4-piperidinyl]methyl]-4(3H)-pyrimidinone
MF C16 H25 N3 O2
INCH InChI=1S/C16H25N3O2/c1-21-9-8-18-6-4-13(5-7-18)11-19-12-17-15(10-16(19)20)14-2-3-14/h10,12-14H,2-9,11H2,1H3
INKY ZVXHSITVUUEKIS-UHFFFAOYSA-N
SR Chemical Catalog
Supplier: Aurora Fine Chemicals
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**PROPERTY DATA AVAILABLE IN THE 'PROP' FORMAT**
L5 ANSWER 14 OF 37 REGISTRY COPYRIGHT 2025 ACS on STN
RN 2201244-29-1 REGISTRY
ED Entered STN: 29 Mar 2018
CN 4(3H)-Pyrimidinone, 6-cyclopropyl-3-[[1-[2-(hexahydro-1H-azepin-1-yl)ethyl]-4-piperidinyl]methyl]- (CA INDEX NAME)
OTHER CA INDEX NAMES:
CN 6-Cyclopropyl-3-[[1-[2-(hexahydro-1H-azepin-1-yl)ethyl]-4-piperidinyl]methyl]-4(3H)-pyrimidinone
MF C21 H34 N4 O
INCH InChI=1S/C21H34N4O/c26-21-15-20(19-5-6-19)22-17-25(21)16-18-7-11-24(12-8-18)14-13-23-9-3-1-2-4-10-23/h15,17-19H,1-14,16H2
INKY RGBQFYPQMSNDQI-UHFFFAOYSA-N
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**PROPERTY DATA AVAILABLE IN THE 'PROP' FORMAT**
L5 ANSWER 15 OF 37 REGISTRY COPYRIGHT 2025 ACS on STN
RN 2200845-05-0 REGISTRY
ED Entered STN: 28 Mar 2018
CN 4(3H)-Pyrimidinone, 6-cyclopropyl-3-[[1-[2-(2-oxo-1(2H)-pyridinyl)ethyl]-4-piperidinyl]methyl]- (CA INDEX NAME)
OTHER CA INDEX NAMES:
CN 6-Cyclopropyl-3-[[1-[2-(2-oxo-1(2H)-pyridinyl)ethyl]-4-piperidinyl]methyl]-4(3H)-pyrimidinone
MF C20 H26 N4 O2
INCH InChI=1S/C20H26N4O2/c25-19-3-1-2-8-23(19)12-11-22-9-6-16(7-10-22)14-24-15-21-18(13-20(24)26)17-4-5-17/h1-3,8,13,15-17H,4-7,9-12,14H2
INKY XUJVNUXBUSOASA-UHFFFAOYSA-N
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**PROPERTY DATA AVAILABLE IN THE 'PROP' FORMAT**
L5 ANSWER 16 OF 37 REGISTRY COPYRIGHT 2025 ACS on STN
RN 2200395-40-8 REGISTRY
ED Entered STN: 28 Mar 2018
CN 4(3H)-Pyrimidinone, 6-cyclopropyl-3-[[1-[2-(1,1-dioxido-2-isothiazolidinyl)ethyl]-4-piperidinyl]methyl]- (CA INDEX NAME)
OTHER CA INDEX NAMES:
CN 6-Cyclopropyl-3-[[1-[2-(1,1-dioxido-2-isothiazolidinyl)ethyl]-4-piperidinyl]methyl]-4(3H)-pyrimidinone
MF C18 H28 N4 O3 S
INCH InChI=1S/C18H28N4O3S/c23-18-12-17(16-2-3-16)19-14-21(18)13-15-4-7-20(8-5-15)9-10-22-6-1-11-26(22,24)25/h12,14-16H,1-11,13H2
INKY PKGXDEKCYZFUEY-UHFFFAOYSA-N
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**PROPERTY DATA AVAILABLE IN THE 'PROP' FORMAT**
L5 ANSWER 17 OF 37 REGISTRY COPYRIGHT 2025 ACS on STN
RN 2199674-57-0 REGISTRY
ED Entered STN: 27 Mar 2018
CN 4(3H)-Pyrimidinone, 6-cyclopropyl-3-[[1-[2-(1H-pyrazol-1-yl)ethyl]-4-piperidinyl]methyl]- (CA INDEX NAME)
OTHER CA INDEX NAMES:
CN 6-Cyclopropyl-3-[[1-[2-(1H-pyrazol-1-yl)ethyl]-4-piperidinyl]methyl]-4(3H)-pyrimidinone
MF C18 H25 N5 O
INCH InChI=1S/C18H25N5O/c24-18-12-17(16-2-3-16)19-14-22(18)13-15-4-8-21(9-5-15)10-11-23-7-1-6-20-23/h1,6-7,12,14-16H,2-5,8-11,13H2
INKY SFHCLVNWZYVLSL-UHFFFAOYSA-N
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**PROPERTY DATA AVAILABLE IN THE 'PROP' FORMAT**
L5 ANSWER 18 OF 37 REGISTRY COPYRIGHT 2025 ACS on STN
RN 2199473-73-7 REGISTRY
ED Entered STN: 26 Mar 2018
CN 4(3H)-Pyrimidinone, 6-cyclopropyl-3-[[1-[2-(2-oxo-1(2H)-pyrazinyl)ethyl]-4-piperidinyl]methyl]- (CA INDEX NAME)
OTHER CA INDEX NAMES:
CN 6-Cyclopropyl-3-[[1-[2-(2-oxo-1(2H)-pyrazinyl)ethyl]-4-piperidinyl]methyl]-4(3H)-pyrimidinone
MF C19 H25 N5 O2
INCH InChI=1S/C19H25N5O2/c25-18-11-17(16-1-2-16)21-14-24(18)13-15-3-6-22(7-4-15)9-10-23-8-5-20-12-19(23)26/h5,8,11-12,14-16H,1-4,6-7,9-10,13H2
INKY WXRDQMAWVARMKK-UHFFFAOYSA-N
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**PROPERTY DATA AVAILABLE IN THE 'PROP' FORMAT**
L5 ANSWER 19 OF 37 REGISTRY COPYRIGHT 2025 ACS on STN
RN 2199473-70-4 REGISTRY
ED Entered STN: 26 Mar 2018
CN 2(1H)-Pyrimidinone, 1-[2-[4-[(4-cyclopropyl-6-oxo-1(6H)-pyrimidinyl)methyl]-1-piperidinyl]ethyl]- (CA INDEX NAME)
OTHER CA INDEX NAMES:
CN 1-[2-[4-[(4-Cyclopropyl-6-oxo-1(6H)-pyrimidinyl)methyl]-1-piperidinyl]ethyl]-2(1H)-pyrimidinone
MF C19 H25 N5 O2
INCH InChI=1S/C19H25N5O2/c25-18-12-17(16-2-3-16)21-14-24(18)13-15-4-8-22(9-5-15)10-11-23-7-1-6-20-19(23)26/h1,6-7,12,14-16H,2-5,8-11,13H2
INKY BZEASCDPAOUVFH-UHFFFAOYSA-N
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**PROPERTY DATA AVAILABLE IN THE 'PROP' FORMAT**
L5 ANSWER 20 OF 37 REGISTRY COPYRIGHT 2025 ACS on STN
RN 2199420-83-0 REGISTRY
ED Entered STN: 26 Mar 2018
CN 1,4-Oxazepin-3(2H)-one, 4-[2-[4-[(4-cyclopropyl-6-oxo-1(6H)-pyrimidinyl)methyl]-1-piperidinyl]ethyl]tetrahydro- (CA INDEX NAME)
OTHER CA INDEX NAMES:
CN 4-[2-[4-[(4-Cyclopropyl-6-oxo-1(6H)-pyrimidinyl)methyl]-1-piperidinyl]ethyl]tetrahydro-1,4-oxazepin-3(2H)-one
MF C20 H30 N4 O3
INCH InChI=1S/C20H30N4O3/c25-19-12-18(17-2-3-17)21-15-24(19)13-16-4-7-22(8-5-16)9-10-23-6-1-11-27-14-20(23)26/h12,15-17H,1-11,13-14H2
INKY NQMXITBQTKKAIZ-UHFFFAOYSA-N
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**PROPERTY DATA AVAILABLE IN THE 'PROP' FORMAT**
L5 ANSWER 21 OF 37 REGISTRY COPYRIGHT 2025 ACS on STN
RN 2199420-81-8 REGISTRY
ED Entered STN: 26 Mar 2018
CN 1,4-Oxazepin-5(2H)-one, 4-[2-[4-[(4-cyclopropyl-6-oxo-1(6H)-pyrimidinyl)methyl]-1-piperidinyl]ethyl]tetrahydro- (CA INDEX NAME)
OTHER CA INDEX NAMES:
CN 4-[2-[4-[(4-Cyclopropyl-6-oxo-1(6H)-pyrimidinyl)methyl]-1-piperidinyl]ethyl]tetrahydro-1,4-oxazepin-5(2H)-one
MF C20 H30 N4 O3
INCH InChI=1S/C20H30N4O3/c25-19-5-11-27-12-10-23(19)9-8-22-6-3-16(4-7-22)14-24-15-21-18(13-20(24)26)17-1-2-17/h13,15-17H,1-12,14H2
INKY YFZKANJDQKPMSU-UHFFFAOYSA-N
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**PROPERTY DATA AVAILABLE IN THE 'PROP' FORMAT**
L5 ANSWER 22 OF 37 REGISTRY COPYRIGHT 2025 ACS on STN
RN 2199344-75-5 REGISTRY
ED Entered STN: 26 Mar 2018
CN 4(3H)-Pyrimidinone, 6-cyclopropyl-3-[[1-[2-(1-methyl-2-piperidinyl)ethyl]-4-piperidinyl]methyl]- (CA INDEX NAME)
OTHER CA INDEX NAMES:
CN 6-Cyclopropyl-3-[[1-[2-(1-methyl-2-piperidinyl)ethyl]-4-piperidinyl]methyl]-4(3H)-pyrimidinone
MF C21 H34 N4 O
INCH InChI=1S/C21H34N4O/c1-23-10-3-2-4-19(23)9-13-24-11-7-17(8-12-24)15-25-16-22-20(14-21(25)26)18-5-6-18/h14,16-19H,2-13,15H2,1H3
INKY VQVJAAJOKCXMDC-UHFFFAOYSA-N
SR Chemical Catalog
Supplier: Aurora Fine Chemicals
LC STN Files: CHEMCATS
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213
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**PROPERTY DATA AVAILABLE IN THE 'PROP' FORMAT**
L5 ANSWER 23 OF 37 REGISTRY COPYRIGHT 2025 ACS on STN
RN 2199343-83-2 REGISTRY
ED Entered STN: 26 Mar 2018
CN 3-Morpholinone, 4-[2-[4-[(4-cyclopropyl-6-oxo-1(6H)-pyrimidinyl)methyl]-1-piperidinyl]ethyl]- (CA INDEX NAME)
OTHER CA INDEX NAMES:
CN 4-[2-[4-[(4-Cyclopropyl-6-oxo-1(6H)-pyrimidinyl)methyl]-1-piperidinyl]ethyl]-3-morpholinone
MF C19 H28 N4 O3
INCH InChI=1S/C19H28N4O3/c24-18-11-17(16-1-2-16)20-14-23(18)12-15-3-5-21(6-4-15)7-8-22-9-10-26-13-19(22)25/h11,14-16H,1-10,12-13H2
INKY FDOIYRPFDBKQTJ-UHFFFAOYSA-N
SR Chemical Catalog
Supplier: Aurora Fine Chemicals
LC STN Files: CHEMCATS
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**PROPERTY DATA AVAILABLE IN THE 'PROP' FORMAT**
L5 ANSWER 24 OF 37 REGISTRY COPYRIGHT 2025 ACS on STN
RN 2199342-95-3 REGISTRY
ED Entered STN: 26 Mar 2018
CN 4(3H)-Pyrimidinone, 6-cyclopropyl-3-[[1-[2-(2-oxo-1-piperidinyl)ethyl]-4-piperidinyl]methyl]- (CA INDEX NAME)
OTHER CA INDEX NAMES:
CN 6-Cyclopropyl-3-[[1-[2-(2-oxo-1-piperidinyl)ethyl]-4-piperidinyl]methyl]-4(3H)-pyrimidinone
MF C20 H30 N4 O2
INCH InChI=1S/C20H30N4O2/c25-19-3-1-2-8-23(19)12-11-22-9-6-16(7-10-22)14-24-15-21-18(13-20(24)26)17-4-5-17/h13,15-17H,1-12,14H2
INKY PSGCKJZWNONELC-UHFFFAOYSA-N
SR Chemical Catalog
Supplier: Aurora Fine Chemicals
LC STN Files: CHEMCATS
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**PROPERTY DATA AVAILABLE IN THE 'PROP' FORMAT**
L5 ANSWER 25 OF 37 REGISTRY COPYRIGHT 2025 ACS on STN
RN 2199275-47-1 REGISTRY
ED Entered STN: 26 Mar 2018
CN 4(3H)-Pyrimidinone, 6-cyclopropyl-3-[[1-[2-(1H-imidazol-1-yl)ethyl]-4-piperidinyl]methyl]- (CA INDEX NAME)
OTHER CA INDEX NAMES:
CN 6-Cyclopropyl-3-[[1-[2-(1H-imidazol-1-yl)ethyl]-4-piperidinyl]methyl]-4(3H)-pyrimidinone
MF C18 H25 N5 O
INCH InChI=1S/C18H25N5O/c24-18-11-17(16-1-2-16)20-14-23(18)12-15-3-6-21(7-4-15)9-10-22-8-5-19-13-22/h5,8,11,13-16H,1-4,6-7,9-10,12H2
INKY OHSFMMVYVKFDEV-UHFFFAOYSA-N
SR Chemical Catalog
Supplier: Aurora Fine Chemicals
LC STN Files: CHEMCATS
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203
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**PROPERTY DATA AVAILABLE IN THE 'PROP' FORMAT**
L5 ANSWER 26 OF 37 REGISTRY COPYRIGHT 2025 ACS on STN
RN 2199275-45-9 REGISTRY
ED Entered STN: 26 Mar 2018
CN 4(3H)-Pyrimidinone, 6-cyclopropyl-3-[[1-[2-(1H-1,2,3-triazol-1-yl)ethyl]-4-piperidinyl]methyl]- (CA INDEX NAME)
OTHER CA INDEX NAMES:
CN 6-Cyclopropyl-3-[[1-[2-(1H-1,2,3-triazol-1-yl)ethyl]-4-piperidinyl]methyl]-4(3H)-pyrimidinone
MF C17 H24 N6 O
INCH InChI=1S/C17H24N6O/c24-17-11-16(15-1-2-15)18-13-22(17)12-14-3-6-21(7-4-14)9-10-23-8-5-19-20-23/h5,8,11,13-15H,1-4,6-7,9-10,12H2
INKY ZFJYCCKZNMUCLR-UHFFFAOYSA-N
SR Chemical Catalog
Supplier: Aurora Fine Chemicals
LC STN Files: CHEMCATS
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466
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**PROPERTY DATA AVAILABLE IN THE 'PROP' FORMAT**
L5 ANSWER 27 OF 37 REGISTRY COPYRIGHT 2025 ACS on STN
RN 2198662-11-0 REGISTRY
ED Entered STN: 25 Mar 2018
CN 4(3H)-Pyrimidinone, 6-cyclopropyl-3-[[1-[2-(4-morpholinyl)ethyl]-4-piperidinyl]methyl]- (CA INDEX NAME)
OTHER CA INDEX NAMES:
CN 6-Cyclopropyl-3-[[1-[2-(4-morpholinyl)ethyl]-4-piperidinyl]methyl]-4(3H)-pyrimidinone
MF C19 H30 N4 O2
INCH InChI=1S/C19H30N4O2/c24-19-13-18(17-1-2-17)20-15-23(19)14-16-3-5-21(6-4-16)7-8-22-9-11-25-12-10-22/h13,15-17H,1-12,14H2
INKY ZNRSRIJVEIHUPZ-UHFFFAOYSA-N
SR Chemical Catalog
Supplier: Aurora Fine Chemicals
LC STN Files: CHEMCATS
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**PROPERTY DATA AVAILABLE IN THE 'PROP' FORMAT**
L5 ANSWER 28 OF 37 REGISTRY COPYRIGHT 2025 ACS on STN
RN 2198369-85-4 REGISTRY
ED Entered STN: 25 Mar 2018
CN 4(3H)-Pyrimidinone, 6-cyclopropyl-3-[[1-[2-(1-methyl-1H-imidazol-2-yl)ethyl]-4-piperidinyl]methyl]- (CA INDEX NAME)
OTHER CA INDEX NAMES:
CN 6-Cyclopropyl-3-[[1-[2-(1-methyl-1H-imidazol-2-yl)ethyl]-4-piperidinyl]methyl]-4(3H)-pyrimidinone
MF C19 H27 N5 O
INCH InChI=1S/C19H27N5O/c1-22-11-7-20-18(22)6-10-23-8-4-15(5-9-23)13-24-14-21-17(12-19(24)25)16-2-3-16/h7,11-12,14-16H,2-6,8-10,13H2,1H3
INKY ANDGRWSUQRGFKF-UHFFFAOYSA-N
SR Chemical Catalog
Supplier: Aurora Fine Chemicals
LC STN Files: CHEMCATS
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**PROPERTY DATA AVAILABLE IN THE 'PROP' FORMAT**
L5 ANSWER 29 OF 37 REGISTRY COPYRIGHT 2025 ACS on STN
RN 2198093-31-9 REGISTRY
ED Entered STN: 25 Mar 2018
CN INDEX NAME NOT YET ASSIGNED
MF C20 H27 N5 O2
INCH InChI=1S/C20H27N5O2/c1-15-10-19(26)24(13-21-15)9-8-23-6-4-16(5-7-23)12-25-14-22-18(11-20(25)27)17-2-3-17/h10-11,13-14,16-17H,2-9,12H2,1H3
INKY MBBKWTNRHQVLNB-UHFFFAOYSA-N
SR Chemical Catalog
Supplier: Aurora Fine Chemicals
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**PROPERTY DATA AVAILABLE IN THE 'PROP' FORMAT**
L5 ANSWER 30 OF 37 REGISTRY COPYRIGHT 2025 ACS on STN
RN 2197882-55-4 REGISTRY
ED Entered STN: 23 Mar 2018
CN 4(3H)-Pyrimidinone, 6-cyclopropyl-3-[[1-[2-(2-methyl-5-oxazolyl)ethyl]-4-piperidinyl]methyl]- (CA INDEX NAME)
OTHER CA INDEX NAMES:
CN 6-Cyclopropyl-3-[[1-[2-(2-methyl-5-oxazolyl)ethyl]-4-piperidinyl]methyl]-4(3H)-pyrimidinone
MF C19 H26 N4 O2
INCH InChI=1S/C19H26N4O2/c1-14-20-11-17(25-14)6-9-22-7-4-15(5-8-22)12-23-13-21-18(10-19(23)24)16-2-3-16/h10-11,13,15-16H,2-9,12H2,1H3
INKY WPSXTOPIYWTQOU-UHFFFAOYSA-N
SR Chemical Catalog
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**PROPERTY DATA AVAILABLE IN THE 'PROP' FORMAT**
L5 ANSWER 31 OF 37 REGISTRY COPYRIGHT 2025 ACS on STN
RN 2197806-90-7 REGISTRY
ED Entered STN: 23 Mar 2018
CN 4(3H)-Pyrimidinone, 6-cyclopropyl-3-[[1-[2-(4-methyl-1H-pyrazol-1-yl)ethyl]-4-piperidinyl]methyl]- (CA INDEX NAME)
OTHER CA INDEX NAMES:
CN 6-Cyclopropyl-3-[[1-[2-(4-methyl-1H-pyrazol-1-yl)ethyl]-4-piperidinyl]methyl]-4(3H)-pyrimidinone
MF C19 H27 N5 O
INCH InChI=1S/C19H27N5O/c1-15-11-21-24(12-15)9-8-22-6-4-16(5-7-22)13-23-14-20-18(10-19(23)25)17-2-3-17/h10-12,14,16-17H,2-9,13H2,1H3
INKY SEZDARSFGPJONR-UHFFFAOYSA-N
SR Chemical Catalog
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**PROPERTY DATA AVAILABLE IN THE 'PROP' FORMAT**
L5 ANSWER 32 OF 37 REGISTRY COPYRIGHT 2025 ACS on STN
RN 2197806-88-3 REGISTRY
ED Entered STN: 23 Mar 2018
CN 4(3H)-Pyrimidinone, 6-cyclopropyl-3-[[1-[2-(1-methyl-1H-pyrazol-5-yl)ethyl]-4-piperidinyl]methyl]- (CA INDEX NAME)
OTHER CA INDEX NAMES:
CN 6-Cyclopropyl-3-[[1-[2-(1-methyl-1H-pyrazol-5-yl)ethyl]-4-piperidinyl]methyl]-4(3H)-pyrimidinone
MF C19 H27 N5 O
INCH InChI=1S/C19H27N5O/c1-22-17(4-8-21-22)7-11-23-9-5-15(6-10-23)13-24-14-20-18(12-19(24)25)16-2-3-16/h4,8,12,14-16H,2-3,5-7,9-11,13H2,1H3
INKY NUYSNHIMGSYFTP-UHFFFAOYSA-N
SR Chemical Catalog
Supplier: Aurora Fine Chemicals
LC STN Files: CHEMCATS
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**PROPERTY DATA AVAILABLE IN THE 'PROP' FORMAT**
L5 ANSWER 33 OF 37 REGISTRY COPYRIGHT 2025 ACS on STN
RN 2197806-86-1 REGISTRY
ED Entered STN: 23 Mar 2018
CN 4(3H)-Pyrimidinone, 6-cyclopropyl-3-[[1-[2-(1H-1,2,4-triazol-1-yl)ethyl]-4-piperidinyl]methyl]- (CA INDEX NAME)
OTHER CA INDEX NAMES:
CN 6-Cyclopropyl-3-[[1-[2-(1H-1,2,4-triazol-1-yl)ethyl]-4-piperidinyl]methyl]-4(3H)-pyrimidinone
MF C17 H24 N6 O
INCH InChI=1S/C17H24N6O/c24-17-9-16(15-1-2-15)19-13-22(17)10-14-3-5-21(6-4-14)7-8-23-12-18-11-20-23/h9,11-15H,1-8,10H2
INKY YQOIYLHEKBLVMC-UHFFFAOYSA-N
SR Chemical Catalog
Supplier: Aurora Fine Chemicals
LC STN Files: CHEMCATS
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208
463
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**PROPERTY DATA AVAILABLE IN THE 'PROP' FORMAT**
L5 ANSWER 34 OF 37 REGISTRY COPYRIGHT 2025 ACS on STN
RN 2197710-87-3 REGISTRY
ED Entered STN: 23 Mar 2018
CN 4(3H)-Pyrimidinone, 6-cyclopropyl-3-[[1-[2-(3-methyl-5-isoxazolyl)ethyl]-4-piperidinyl]methyl]- (CA INDEX NAME)
OTHER CA INDEX NAMES:
CN 6-Cyclopropyl-3-[[1-[2-(3-methyl-5-isoxazolyl)ethyl]-4-piperidinyl]methyl]-4(3H)-pyrimidinone
MF C19 H26 N4 O2
INCH InChI=1S/C19H26N4O2/c1-14-10-17(25-21-14)6-9-22-7-4-15(5-8-22)12-23-13-20-18(11-19(23)24)16-2-3-16/h10-11,13,15-16H,2-9,12H2,1H3
INKY FUMILYATIJWUDV-UHFFFAOYSA-N
SR Chemical Catalog
Supplier: Aurora Fine Chemicals
LC STN Files: CHEMCATS
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**PROPERTY DATA AVAILABLE IN THE 'PROP' FORMAT**
L5 ANSWER 35 OF 37 REGISTRY COPYRIGHT 2025 ACS on STN
RN 2197639-66-8 REGISTRY
ED Entered STN: 23 Mar 2018
CN 4(3H)-Pyrimidinone, 6-cyclopropyl-3-[[1-(3,3,3-trifluoro-2-hydroxypropyl)-4-piperidinyl]methyl]- (CA INDEX NAME)
OTHER CA INDEX NAMES:
CN 6-Cyclopropyl-3-[[1-(3,3,3-trifluoro-2-hydroxypropyl)-4-piperidinyl]methyl]-4(3H)-pyrimidinone
MF C16 H22 F3 N3 O2
INCH InChI=1S/C16H22F3N3O2/c17-16(18,19)14(23)9-21-5-3-11(4-6-21)8-22-10-20-13(7-15(22)24)12-1-2-12/h7,10-12,14,23H,1-6,8-9H2
INKY WUFWETNHIYEGQB-UHFFFAOYSA-N
SR Chemical Catalog
Supplier: Aurora Fine Chemicals
LC STN Files: CHEMCATS
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196
439
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**PROPERTY DATA AVAILABLE IN THE 'PROP' FORMAT**
L5 ANSWER 36 OF 37 REGISTRY COPYRIGHT 2025 ACS on STN
RN 2189434-08-8 REGISTRY
ED Entered STN: 12 Mar 2018
CN 4(3H)-Pyrimidinone, 6-cyclopropyl-3-[[1-(2-methylpropyl)-4-piperidinyl]methyl]- (CA INDEX NAME)
OTHER CA INDEX NAMES:
CN 6-Cyclopropyl-3-[[1-(2-methylpropyl)-4-piperidinyl]methyl]-4(3H)-pyrimidinone
MF C17 H27 N3 O
INCH InChI=1S/C17H27N3O/c1-13(2)10-19-7-5-14(6-8-19)11-20-12-18-16(9-17(20)21)15-3-4-15/h9,12-15H,3-8,10-11H2,1-2H3
INKY MHMUSKAHXDCBIW-UHFFFAOYSA-N
SR Chemical Library
Supplier: Aurora Fine Chemicals
LC STN Files: CHEMCATS
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**PROPERTY DATA AVAILABLE IN THE 'PROP' FORMAT**
L5 ANSWER 37 OF 37 REGISTRY COPYRIGHT 2025 ACS on STN
RN 2097924-20-2 REGISTRY
ED Entered STN: 08 Jun 2017
CN 4(3H)-Pyrimidinone, 6-cyclopropyl-3-[[1-[2-(2,3-dihydro-5-benzofuranyl)ethyl]-4-piperidinyl]methyl]- (CA INDEX NAME)
OTHER CA INDEX NAMES:
CN 6-Cyclopropyl-3-[[1-[2-(2,3-dihydro-5-benzofuranyl)ethyl]-4-piperidinyl]methyl]-4(3H)-pyrimidinone
MF C23 H29 N3 O2
INCH InChI=1S/C23H29N3O2/c27-23-14-21(19-2-3-19)24-16-26(23)15-18-6-10-25(11-7-18)9-5-17-1-4-22-20(13-17)8-12-28-22/h1,4,13-14,16,18-19H,2-3,5-12,15H2
INKY HALBSXBKHXHGIV-UHFFFAOYSA-N
SR Chemical Catalog
Supplier: Life Chemicals, Inc.
LC STN Files: CHEMCATS
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Please note that instant claim 20 is included in the rejection because, while claim 20 further limits compounds of claim 14 when R1 or R2 represents an aryl group, the claim does not require that R1 or R2 represents an aryl group.
Claim Rejections - 35 USC § 103
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, 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.
The factual inquiries for establishing a background for determining obviousness under 35 U.S.C. 103 are summarized as follows:
1. Determining the scope and contents of the prior art.
2. Ascertaining the differences between the prior art and the claims at issue.
3. Resolving the level of ordinary skill in the pertinent art.
4. Considering objective evidence present in the application indicating obviousness or nonobviousness.
The factual inquiries for establishing a background for determining obviousness under 35 U.S.C. 103 are summarized as follows:
1. Determining the scope and contents of the prior art.
2. Ascertaining the differences between the prior art and the claims at issue.
3. Resolving the level of ordinary skill in the pertinent art.
4. Considering objective evidence present in the application indicating obviousness or nonobviousness.
Claims 14-20 and 23 are rejected under 35 U.S.C. 103 as being unpatentable over Sandoz (GB858792A; published 1961; cited in IDS).
Sandoz discloses pharmaceutical compounds having the formula (see page 1, left side):
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In particular, Sandoz discloses in Example 8 (page 5) and claim 6 (page 8) the compound 1-(N-methyl-piperidyl-4)-3-phenyl-5-methyl-pyridazone-6 and its monohydrochloride:
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.
Sandoz’s compound reads on R1 (phenyl), R2 (H), R5 (H), Y (C-Me), X (N), n (0), m (0), and m’ (1) of instant formula (I).
Sandoz’s compound differs from instant formula (I) by the group R3, which is H in Sandoz’s compound but cannot be H in the instant claims.
However, the instant claims also include compounds wherein R3 is a C1-C6 alkyl. Such compounds are homologs of Sandoz’s compound. MPEP 2144.09, second paragraph, states, “Compounds which are position isomers or homologs are generally of sufficiently close structural similarity that there is a presumed expectation that such compounds possess similar properties.” In re Wilder, 563 F.2d 457, 195 USPQ 426 (CCPA 1977). The homolog is expected to be preparable by the same method and to have generally the same properties. This expectation is then deemed the motivation for preparing the homolog. This circumstance has arisen many times. See In re Schechter and LaForge, 98 USPQ 144, 150, which states “a novel useful chemical compound which is homologous or isomeric with compounds of the prior art is unpatentable unless it possesses some unobvious or unexpected beneficial property not possessed by the prior art compounds.” See In re Wilder, 166 USPQ 545, 548. Note also In re Deuel 34 USPQ2d 1210, 1214 which states, “Structural relationships may provide the requisite motivation or suggestion to modify known compounds to obtain new compounds … a known compound may suggest its analogs or isomers, either geometric isomers (cis v. trans) or position isomers (e.g., ortho v. para).”
Please also note that Sandoz teaches that R1 in the general formula:
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can be is a “lower alkyl group”, which is defined as an alkyl group containing 4 or less carbon atoms. Accordingly, compounds which are homologs of 1-(N-methyl-piperidyl-4)-3-phenyl-5-methyl-pyridazone-6, such as:
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,
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,
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would have been expected by the skilled artisan to possess similar properties to the compound disclosed by Sandoz.
Accordingly, compounds reading on instant claims 14-20, having similar structure and the same utility as the compounds in Sandoz, would have been prima facie obvious before the effective filing date of the instant application. A skilled artisan would have been motivated to prepare a position isomer of the compounds recited in Sandoz with a reasonable expectation of success to obtain a compound with the same utility.
With respect to claim 23, Sandoz discloses that the compounds therein possess pharmacodynamic properties, and discloses that the hydrochloride salts are easily soluble in water (page 2, right side). Further, Sandoz discloses a composition comprising the hydrochloride salt of Sandoz’s compound and ethanol; and discloses a composition comprising the hydrochloride salt of Sandoz’s compound and water (page 5, Example 8, lines 49-47).
It would have therefore been prima facie obvious to prepare a pharmaceutical composition comprising the aforementioned compounds and a pharmaceutically acceptable support in view of Sandoz’s teaching that such compounds have pharmaceutical utility.
Allowable Subject Matter
Claims 21-22 are objected to as being dependent upon a rejected base claim, but would be allowable if rewritten in independent form including all of the limitations of the base claim and any intervening claims.
Conclusion
Claims 21-22 are objected to. Claims 14-20 and 23 are rejected. Claims 24-25 are withdrawn.
Applicant's amendment necessitated the new ground(s) of rejection presented in this Office action. Accordingly, THIS ACTION IS MADE FINAL. See MPEP § 706.07(a). Applicant is reminded of the extension of time policy as set forth in 37 CFR 1.136(a).
A shortened statutory period for reply to this final action is set to expire THREE MONTHS from the mailing date of this action. In the event a first reply is filed within TWO MONTHS of the mailing date of this final action and the advisory action is not mailed until after the end of the THREE-MONTH shortened statutory period, then the shortened statutory period will expire on the date the advisory action is mailed, and any nonprovisional extension fee (37 CFR 1.17(a)) pursuant to 37 CFR 1.136(a) will be calculated from the mailing date of the advisory action. In no event, however, will the statutory period for reply expire later than SIX MONTHS from the mailing date of this final action.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to Kyle Nottingham whose telephone number is (571)270-0640. The examiner can normally be reached M-F from 8:30 am - 5:30 pm.
Examiner interviews are available via telephone, in-person, and video conferencing using a USPTO supplied web-based collaboration tool. To schedule an interview, applicant is encouraged to use the USPTO Automated Interview Request (AIR) at http://www.uspto.gov/interviewpractice.
If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Clinton Brooks can be reached at (571) 270-7682. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
Information regarding the status of published or unpublished applications may be obtained from Patent Center. Unpublished application information in Patent Center is available to registered users. To file and manage patent submissions in Patent Center, visit: https://patentcenter.uspto.gov. Visit https://www.uspto.gov/patents/apply/patent-center for more information about Patent Center and https://www.uspto.gov/patents/docx for information about filing in DOCX format. For additional questions, contact the Electronic Business Center (EBC) at 866-217-9197 (toll-free). If you would like assistance from a USPTO Customer Service Representative, call 800-786-9199 (IN USA OR CANADA) or 571-272-1000.
/K.N./Examiner, Art Unit 1621
/CLINTON A BROOKS/Supervisory Patent Examiner, Art Unit 1621