http://rdf.ncbi.nlm.nih.gov/pubchem/patent/AR-120556-A1
Outgoing Links
| Predicate | Object |
|---|---|
| assignee | http://rdf.ncbi.nlm.nih.gov/pubchem/patentassignee/MD5_0597f9c318d2aeca86db94711c516383 |
| classificationCPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/A61P3-06 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D513-04 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D487-04 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/A61K31-519 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D498-04 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/A61P3-00 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/A61P1-16 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/A61P3-10 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/A61P9-00 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/A61P3-04 |
| classificationIPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D513-04 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D487-04 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D498-04 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/A61P9-00 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/A61P3-00 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/A61K31-519 |
| filingDate | 2020-11-25-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| inventor | http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_d8cb386881dde5b49936656598700139 http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_08fc627da1f83a7e51194561b4240003 http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_060d732728968328027148a21f3660f2 http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_90cd152ea8609c6c7e04ba77a7405938 http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_47a8a314fbbe962d6d108700135fe1ee http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_549c84cbd0b05f3d1d924aad619ad827 http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_ef8f1989a7d5ec6d1cbb4e077c19d800 |
| publicationDate | 2022-02-23-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationNumber | AR-120556-A1 |
| titleOfInvention | HETEROCYCLIC COMPOUNDS AS DELTA-5 DESATURASE INHIBITORS AND METHODS OF USE |
| abstract | The present disclosure provides compounds useful for the inhibition of Delta-5 Desaturase ("D5D"). The compounds have a general formula (1) in which the variables of formula (1) are defined herein. This disclosure also provides pharmaceutical compositions comprising the compounds, uses of the compounds, and compositions for the treatment of, for example, a cardiovascular or metabolic disorder. Furthermore, the disclosure provides useful intermediates in the synthesis of compounds of formula (1). Claim 1: A compound of formula [1] or a tautomer thereof, or a pharmaceutically acceptable salt of said compound or said tautomer, wherein the group of formula [2] together with the N atom and the C atom al which is bonded forms a 5-membered ring, wherein the ring is aromatic, unsaturated, partially saturated, or saturated; x, y, and z are independently selected from CR, CRR', N, NR'', O, S(O)ₙ, C=O, C=S and C=NH; each R and R' are independently selected from H, halogen, -OH, -CN, -CO(C₁₋₄ alkyl), -S(O)ₙ(C₁₋₄ alkyl), -COOH, -COO(C₁₋ alkyl ₄), -CONH₂, -CONH(C₁₋₄ alkyl), -CO(C₁₋₄ dialkylamino), -NH₂, C₁₋₄ alkylamino, C₁₋₄ dialkylamino, -NH(CO-C₁₋₄ alkyl), -N (C₁₋₄-alkyl)C(=O)F, C₁₋₄-alkyl, -(CH₂)ₘ(C₃₋₅-cycloalkyl), -CH₂(C₃₋₅-heterocycloalkyl), C₁₋₄-deuteroalkyl, C₃₋₅-cycloalkyl, heterocycloalkyl C₃₋₄, C₂₋₄ alkenyl, C₂₋₄ alkynyl, C₁₋₄ alkoxy, C₁₋₄ deuteroalkoxy, phenyl, 5-membered heteroaryl and 6-membered heteroaryl; wherein the C₁₋₄ alkyl group is optionally substituted with 1 to 4 F or optionally substituted with a substituent selected from -OH, -CN, C₁₋₄ alkoxy, -NH₂, C₁₋₄ alkylamino, C₁₋₄ dialkylamino and -S(O)ₙ(C₁₋₄ alkyl); wherein the C₁₋₄ alkoxy group is optionally substituted with 1 to 4 independently selected halogens or optionally substituted with a substituent selected from -OH, -CN, C₁₋₄ alkoxy, -NH₂, C₁₋₄ alkylamino, C₁₋ dialkylamino ₄ and -S(O)ₙ(C₁₋₄ alkyl); wherein the -CH₂(C₃₋₅-cycloalkyl), C₃₋₄-heterocycloalkyl, phenyl, 5-membered heteroaryl and 6-membered heteroaryl groups are optionally substituted with 1 to 4 substituents independently selected from halogen, -OH, -CN, C₁₋₄ alkoxy, C₁₋₄ alkyl, -NH₂, C₁₋₄ alkylamino, C₁₋₄ dialkylamino, and -S(O)ₙ(C₁₋₄ alkyl); and wherein R of a first CR or CRR' group and R of a second CR or CRR' group, if present, together with the atoms to which they are attached, form a C₃₋₅ carbocycle; each R'' is independently selected from H, -OH, -CO(C₁₋₄ alkyl), -S(O)ₙ(C₁₋₄ alkyl), -COO(C₁₋₄ alkyl), -CONH₂, -CONH( C₁₋₄ alkyl), -CO(C₁₋₄ dialkylamino), C₁₋₄ alkyl, -(CH₂)ₘ(C₃₋₅ cycloalkyl), -CH₂(C₃₋₅ heterocycloalkyl), C₁₋₄ deuteroalkyl, C₃₋₅ cycloalkyl , C₃₋₄ heterocycloalkyl, C₂₋₄ alkenyl, C₂₋₄ alkynyl, phenyl, 5-membered heteroaryl and 6-membered heteroaryl; wherein the C₁₋₄ alkyl group is optionally substituted with 1 to 4 F or optionally substituted with a substituent selected from -OH, -CN, C₁₋₄ alkoxy, -NH₂, C₁₋₄ alkylamino, C₁₋₄ dialkylamino and -S(O)ₙ(C₁₋₄ alkyl); and wherein the -(CH₂)ₘ(C₃₋₅-cycloalkyl), C₃₋₄-heterocycloalkyl, phenyl, 5-membered heteroaryl, and 6-membered heteroaryl groups are optionally substituted with 1 to 4 substituents independently selected from halogen, -OH , -CN, C₁₋₄ alkoxy, C₁₋₄ alkyl, -NH₂, C₁₋₄ alkylamino, C₁₋₄ dialkylamino, and -S(O)ₙ(C₁₋₄ alkyl); R¹ is O, S or NH; R² is a compound of formula [3], [4] or [5], in which ring A is a 5-membered heteroaryl containing one heteroatom selected from N, S and O and optionally one or two additional N atoms the remaining ring atoms of the 5-membered heteroaryl being carbon, wherein i) ring A is attached via a C atom to the bicyclic nucleus and R³ is attached via an N atom; or ii) ring A is attached via an N atom to the bicyclic nucleus and R³ is attached via a C atom; or iii) ring A is attached via a C atom to the bicyclic nucleus and R³ is attached via a C atom; and wherein the portion, selected from the group of formulas [6] of R² is optionally substituted with one or two independently selected substituents R³'; R³ is C₁₋₆ alkyl, C₃₋₅ cycloalkyl, C₂₋₆ alkoxy, C₁₋₆ alkylamino, C₁₋₆ dialkylamino, -S(O)ₙ(C₁₋₆ alkyl), -CH₂(C₃₋₅ cycloalkyl), - OCH₂(C₃₋₅-cycloalkyl), -NHCH₂(C₃₋₅-cycloalkyl), -S(O)ₙCH₂(C₃₋₅-cycloalkyl), -CH₂(C₃₋₅-heterocycloalkyl), or phenyl; in which C 19 alkyl, C 3 9 cycloalkyl, C 2 6 alkoxy, C 1 6 alkylamino, C 1 9 dialkylamino, -S(O) 3 (C 1 9 alkyl), -CH 2 (C 3 9 cycloalkyl) ), -OCH₂(C₃₋₅ cycloalkyl), -NHCH₂(C₃₋₅ cycloalkyl), and -S(O)ₙCH₂(C₃₋₅ cycloalkyl) are optionally substituted with 1-9 halogen atoms and are optionally substituted with -CN and wherein phenyl is optionally substituted with 1-3 substituents selected from halogen, C₁₋₄ alkyl, C₁₋₄ haloalkyl, C₁₋₄ alkoxy, and C₁₋₄ haloalkoxy; R³' is independently halogen, C₁₋₄ alkyl, C₁₋₄ haloalkyl, C₁₋₄ alkoxy, or C₁₋₄ haloalkoxy; R⁴ is C₁₋₃ alkyl, C₁₋₄ haloalkyl, C₁₋₄ alkoxy, C₁₋₄ haloalkoxy, C₃₋₅ cycloalkyl or C₃₋₅ cyclohaloalkyl; n is 0, 1 or 2; and m is 1 or 2; provided that (1) if the compound of formula [1] is a compound of formula [7] then R² is not the compound of formula [4]; (2) if the compound of formula [1] is a compound of formula [8] then R² is not the compound of formula [4]; (3) if the compound of formula [1] is a compound of formula [9] or [10] then R² is not the compound of formula [4]; and (4) if any of R, R' or R'' is phenyl then R³ is not unsubstituted C₁₋₆ alkyl and R³ is not C₁₋₂ alkoxy. |
| priorityDate | 2019-11-25-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| type | http://data.epo.org/linked-data/def/patent/Publication |
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