ES2964299T3 - Derivados de pirrolidinona como agonistas del receptor del péptido formilado 2 - Google Patents
Derivados de pirrolidinona como agonistas del receptor del péptido formilado 2 Download PDFInfo
- Publication number
- ES2964299T3 ES2964299T3 ES19818484T ES19818484T ES2964299T3 ES 2964299 T3 ES2964299 T3 ES 2964299T3 ES 19818484 T ES19818484 T ES 19818484T ES 19818484 T ES19818484 T ES 19818484T ES 2964299 T3 ES2964299 T3 ES 2964299T3
- Authority
- ES
- Spain
- Prior art keywords
- difluoro
- methoxyphenyl
- amino
- oxadiazol
- pyrrolidin
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 108090000765 processed proteins & peptides Proteins 0.000 title description 5
- 150000004040 pyrrolidinones Chemical class 0.000 title description 3
- 229940044601 receptor agonist Drugs 0.000 title description 2
- 239000000018 receptor agonist Substances 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 75
- 239000000203 mixture Substances 0.000 claims abstract description 66
- 238000011282 treatment Methods 0.000 claims abstract description 25
- 206010019280 Heart failures Diseases 0.000 claims abstract description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 33
- 125000000217 alkyl group Chemical group 0.000 claims description 31
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 26
- -1 benzoisoxazolyl Chemical group 0.000 claims description 22
- 125000001188 haloalkyl group Chemical group 0.000 claims description 20
- 125000001424 substituent group Chemical group 0.000 claims description 20
- 125000004076 pyridyl group Chemical group 0.000 claims description 16
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 15
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 15
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 12
- 239000003937 drug carrier Substances 0.000 claims description 9
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 9
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 8
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 7
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 7
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 6
- 125000004414 alkyl thio group Chemical group 0.000 claims description 6
- 125000004440 haloalkylsulfinyl group Chemical group 0.000 claims description 6
- 125000004995 haloalkylthio group Chemical group 0.000 claims description 6
- 208000019622 heart disease Diseases 0.000 claims description 6
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 6
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 6
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 208000010125 myocardial infarction Diseases 0.000 claims description 5
- 230000001154 acute effect Effects 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- 206010002383 Angina Pectoris Diseases 0.000 claims description 2
- 206010002388 Angina unstable Diseases 0.000 claims description 2
- 206010007558 Cardiac failure chronic Diseases 0.000 claims description 2
- 208000007814 Unstable Angina Diseases 0.000 claims description 2
- 125000005872 benzooxazolyl group Chemical group 0.000 claims description 2
- 230000003683 cardiac damage Effects 0.000 claims description 2
- 208000029078 coronary artery disease Diseases 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 230000000642 iatrogenic effect Effects 0.000 claims description 2
- 201000004332 intermediate coronary syndrome Diseases 0.000 claims description 2
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 2
- 238000002560 therapeutic procedure Methods 0.000 claims description 2
- 125000001475 halogen functional group Chemical group 0.000 claims 13
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 10
- FQQPYSJQTPOTAI-KKSFZXQISA-N (3S,4R)-3-[[5-[4-(4-chloropyridin-2-yl)oxyphenyl]-1,3,4-oxadiazol-2-yl]amino]-4-(2,6-difluoro-4-methoxyphenyl)pyrrolidin-2-one Chemical compound COC1=CC(F)=C([C@H](CNC2=O)[C@@H]2NC2=NN=C(C(C=C3)=CC=C3OC3=NC=CC(Cl)=C3)O2)C(F)=C1 FQQPYSJQTPOTAI-KKSFZXQISA-N 0.000 claims 1
- HZPUAXBCDQXVJS-XOBRGWDASA-N (3S,4R)-3-[[5-[4-(5-chloropyrazin-2-yl)oxyphenyl]-1,3,4-oxadiazol-2-yl]amino]-4-(2,6-difluoro-4-methoxyphenyl)pyrrolidin-2-one Chemical compound COC1=CC(F)=C([C@H](CNC2=O)[C@@H]2NC2=NN=C(C(C=C3)=CC=C3OC(C=N3)=NC=C3Cl)O2)C(F)=C1 HZPUAXBCDQXVJS-XOBRGWDASA-N 0.000 claims 1
- QFWADSLRJZHARC-LRDDRELGSA-N (3S,4R)-4-(2,6-difluoro-4-methoxyphenyl)-3-[(5-phenyl-1,3,4-oxadiazol-2-yl)amino]pyrrolidin-2-one Chemical compound COC1=CC(F)=C([C@H](CNC2=O)[C@@H]2NC2=NN=C(C3=CC=CC=C3)O2)C(F)=C1 QFWADSLRJZHARC-LRDDRELGSA-N 0.000 claims 1
- JOBIFNPDLOIIHK-NHYWBVRUSA-N (3S,4R)-4-(2,6-difluoro-4-methoxyphenyl)-3-[(5-pyridin-3-yl-1,3,4-oxadiazol-2-yl)amino]pyrrolidin-2-one Chemical compound COC1=CC(=C(C(=C1)F)[C@@H]2CNC(=O)[C@H]2NC3=NN=C(O3)C4=CN=CC=C4)F JOBIFNPDLOIIHK-NHYWBVRUSA-N 0.000 claims 1
- CASLQEKLSGVNHL-QFYYESIMSA-N (3S,4R)-4-(2,6-difluoro-4-methoxyphenyl)-3-[[5-(3,4-difluorophenyl)-1,3,4-oxadiazol-2-yl]amino]pyrrolidin-2-one Chemical compound COC1=CC(=C(C(=C1)F)[C@@H]2CNC(=O)[C@H]2NC3=NN=C(O3)C4=CC(=C(C=C4)F)F)F CASLQEKLSGVNHL-QFYYESIMSA-N 0.000 claims 1
- WMMWDGZLOMURSR-KXBFYZLASA-N (3S,4R)-4-(2,6-difluoro-4-methoxyphenyl)-3-[[5-(4-propan-2-yloxyphenyl)-1,3,4-oxadiazol-2-yl]amino]pyrrolidin-2-one Chemical compound CC(C)OC(C=C1)=CC=C1C1=NN=C(N[C@@H]([C@@H](CN2)C(C(F)=CC(OC)=C3)=C3F)C2=O)O1 WMMWDGZLOMURSR-KXBFYZLASA-N 0.000 claims 1
- AOPILQFKSGKVMG-YWZLYKJASA-N (3S,4R)-4-(2,6-difluoro-4-methoxyphenyl)-3-[[5-(4-pyrazin-2-yloxyphenyl)-1,3,4-oxadiazol-2-yl]amino]pyrrolidin-2-one Chemical compound COC1=CC(=C(C(=C1)F)[C@@H]2CNC(=O)[C@H]2NC3=NN=C(O3)C4=CC=C(C=C4)OC5=NC=CN=C5)F AOPILQFKSGKVMG-YWZLYKJASA-N 0.000 claims 1
- JZLGGFBCIRGBER-KXBFYZLASA-N (3S,4R)-4-(2,6-difluoro-4-methoxyphenyl)-3-[[5-(4-pyrazol-1-ylphenyl)-1,3,4-oxadiazol-2-yl]amino]pyrrolidin-2-one Chemical compound COC1=CC(F)=C([C@H](CNC2=O)[C@@H]2NC2=NN=C(C(C=C3)=CC=C3N3N=CC=C3)O2)C(F)=C1 JZLGGFBCIRGBER-KXBFYZLASA-N 0.000 claims 1
- PHOXLGFLDWJHCA-LRDDRELGSA-N (3S,4R)-4-(2,6-difluoro-4-methoxyphenyl)-3-[[5-[4-(1,1,2,2,2-pentafluoroethylsulfanyl)phenyl]-1,3,4-oxadiazol-2-yl]amino]pyrrolidin-2-one Chemical compound COC1=CC(F)=C([C@H](CNC2=O)[C@@H]2NC2=NN=C(C(C=C3)=CC=C3SC(C(F)(F)F)(F)F)O2)C(F)=C1 PHOXLGFLDWJHCA-LRDDRELGSA-N 0.000 claims 1
- GGIOXHKVQKXKKT-YWZLYKJASA-N (3S,4R)-4-(2,6-difluoro-4-methoxyphenyl)-3-[[5-[4-(3-fluoropyridin-2-yl)oxyphenyl]-1,3,4-oxadiazol-2-yl]amino]pyrrolidin-2-one Chemical compound COC1=CC(F)=C([C@H](CNC2=O)[C@@H]2NC2=NN=C(C(C=C3)=CC=C3OC3=NC=CC=C3F)O2)C(F)=C1 GGIOXHKVQKXKKT-YWZLYKJASA-N 0.000 claims 1
- UGEXERHFIFJZDN-KKSFZXQISA-N (3S,4R)-4-(2,6-difluoro-4-methoxyphenyl)-3-[[5-[4-(5-fluoropyridin-2-yl)oxyphenyl]-1,3,4-oxadiazol-2-yl]amino]pyrrolidin-2-one Chemical compound COC1=CC(F)=C([C@H](CNC2=O)[C@@H]2NC2=NN=C(C(C=C3)=CC=C3OC(C=C3)=NC=C3F)O2)C(F)=C1 UGEXERHFIFJZDN-KKSFZXQISA-N 0.000 claims 1
- VWYWDOAVLRMAQI-BTYIYWSLSA-N (3S,4R)-4-(2,6-difluoro-4-methoxyphenyl)-3-[[5-[4-(6-fluoropyridin-2-yl)oxyphenyl]-1,3,4-oxadiazol-2-yl]amino]pyrrolidin-2-one Chemical compound COC1=CC(F)=C([C@H](CNC2=O)[C@@H]2NC2=NN=C(C(C=C3)=CC=C3OC3=NC(F)=CC=C3)O2)C(F)=C1 VWYWDOAVLRMAQI-BTYIYWSLSA-N 0.000 claims 1
- SVPBEBBDLBXAIE-AOMKIAJQSA-N (3S,4R)-4-(2,6-difluoro-4-methoxyphenyl)-3-[[5-[4-(6-methoxypyridin-2-yl)oxyphenyl]-1,3,4-oxadiazol-2-yl]amino]pyrrolidin-2-one Chemical compound COC1=CC(F)=C([C@H](CNC2=O)[C@@H]2NC2=NN=C(C(C=C3)=CC=C3OC3=NC(OC)=CC=C3)O2)C(F)=C1 SVPBEBBDLBXAIE-AOMKIAJQSA-N 0.000 claims 1
- BQLBNKFAODICPQ-BTYIYWSLSA-N (3S,4R)-4-(2,6-difluoro-4-methoxyphenyl)-3-[[5-[4-(6-methoxypyrimidin-4-yl)oxyphenyl]-1,3,4-oxadiazol-2-yl]amino]pyrrolidin-2-one Chemical compound COC1=CC(=C(C(=C1)F)[C@@H]2CNC(=O)[C@H]2NC3=NN=C(O3)C4=CC=C(C=C4)OC5=NC=NC(=C5)OC)F BQLBNKFAODICPQ-BTYIYWSLSA-N 0.000 claims 1
- IWTHSFWNUSKGFL-KKSFZXQISA-N (3S,4R)-4-(2,6-difluoro-4-methoxyphenyl)-3-[[5-[4-(6-methylpyrazin-2-yl)oxyphenyl]-1,3,4-oxadiazol-2-yl]amino]pyrrolidin-2-one Chemical compound CC1=CN=CC(OC(C=C2)=CC=C2C2=NN=C(N[C@@H]([C@@H](CN3)C(C(F)=CC(OC)=C4)=C4F)C3=O)O2)=N1 IWTHSFWNUSKGFL-KKSFZXQISA-N 0.000 claims 1
- OPZOIJLIYGVUET-LRDDRELGSA-N (3S,4R)-4-(2,6-difluoro-4-methoxyphenyl)-3-[[5-[4-(difluoromethoxy)phenyl]-1,3,4-oxadiazol-2-yl]amino]pyrrolidin-2-one Chemical compound COC1=CC(F)=C([C@H](CNC2=O)[C@@H]2NC2=NN=C(C(C=C3)=CC=C3OC(F)F)O2)C(F)=C1 OPZOIJLIYGVUET-LRDDRELGSA-N 0.000 claims 1
- YDBADFVDSDJNFM-LRDDRELGSA-N (3S,4R)-4-(2,6-difluoro-4-methoxyphenyl)-3-[[5-[4-(difluoromethyl)phenyl]-1,3,4-oxadiazol-2-yl]amino]pyrrolidin-2-one Chemical compound COC1=CC(=C(C(=C1)F)[C@@H]2CNC(=O)[C@H]2NC3=NN=C(O3)C4=CC=C(C=C4)C(F)F)F YDBADFVDSDJNFM-LRDDRELGSA-N 0.000 claims 1
- RJCAQJAXHDHBIQ-LRDDRELGSA-N (3S,4R)-4-(2,6-difluoro-4-methoxyphenyl)-3-[[5-[4-(difluoromethylsulfanyl)phenyl]-1,3,4-oxadiazol-2-yl]amino]pyrrolidin-2-one Chemical compound COC1=CC(F)=C([C@H](CNC2=O)[C@@H]2NC2=NN=C(C(C=C3)=CC=C3SC(F)F)O2)C(F)=C1 RJCAQJAXHDHBIQ-LRDDRELGSA-N 0.000 claims 1
- RUZUBSJPMWAWOJ-LRDDRELGSA-N (3S,4R)-4-(2,6-difluoro-4-methoxyphenyl)-3-[[5-[4-(trifluoromethoxy)phenyl]-1,3,4-oxadiazol-2-yl]amino]pyrrolidin-2-one Chemical compound COC1=CC(=C(C(=C1)F)[C@@H]2CNC(=O)[C@H]2NC3=NN=C(O3)C4=CC=C(C=C4)OC(F)(F)F)F RUZUBSJPMWAWOJ-LRDDRELGSA-N 0.000 claims 1
- XLKARCVDHKWCKS-LRDDRELGSA-N (3S,4R)-4-(2,6-difluoro-4-methoxyphenyl)-3-[[5-[4-(trifluoromethyl)phenyl]-1,3,4-oxadiazol-2-yl]amino]pyrrolidin-2-one Chemical compound COC1=CC(=C(C(=C1)F)[C@@H]2CNC(=O)[C@H]2NC3=NN=C(O3)C4=CC=C(C=C4)C(F)(F)F)F XLKARCVDHKWCKS-LRDDRELGSA-N 0.000 claims 1
- WWJRZATUTTWCDT-LRDDRELGSA-N (3S,4R)-4-(2,6-difluoro-4-methoxyphenyl)-3-[[5-[4-(trifluoromethylsulfanyl)phenyl]-1,3,4-oxadiazol-2-yl]amino]pyrrolidin-2-one Chemical compound COC1=CC(F)=C([C@H](CNC2=O)[C@@H]2NC2=NN=C(C(C=C3)=CC=C3SC(F)(F)F)O2)C(F)=C1 WWJRZATUTTWCDT-LRDDRELGSA-N 0.000 claims 1
- QFUCDGWBZZLKIU-KKSFZXQISA-N (3S,4R)-4-(2,6-difluoro-4-methoxyphenyl)-3-[[5-[4-[6-(trifluoromethyl)pyridin-3-yl]oxyphenyl]-1,3,4-oxadiazol-2-yl]amino]pyrrolidin-2-one Chemical compound COC1=CC(F)=C([C@H](CNC2=O)[C@@H]2NC2=NN=C(C(C=C3)=CC=C3OC3=CC=C(C(F)(F)F)N=C3)O2)C(F)=C1 QFUCDGWBZZLKIU-KKSFZXQISA-N 0.000 claims 1
- FEHASKVSTUQUNL-BONVTDFDSA-N (3S,4R)-4-(2,6-difluoro-4-methoxyphenyl)-3-[[5-[5-(trifluoromethyl)pyridin-2-yl]-1,3,4-oxadiazol-2-yl]amino]pyrrolidin-2-one Chemical compound COC1=CC(=C(C(=C1)F)[C@@H]2CNC(=O)[C@H]2NC3=NN=C(O3)C4=NC=C(C=C4)C(F)(F)F)F FEHASKVSTUQUNL-BONVTDFDSA-N 0.000 claims 1
- SLBSBNFODNNEFZ-BONVTDFDSA-N (3S,4R)-4-(2,6-difluoro-4-methoxyphenyl)-3-[[5-[6-(trifluoromethyl)pyridin-3-yl]-1,3,4-oxadiazol-2-yl]amino]pyrrolidin-2-one Chemical compound COC1=CC(=C(C(=C1)F)[C@@H]2CNC(=O)[C@H]2NC3=NN=C(O3)C4=CN=C(C=C4)C(F)(F)F)F SLBSBNFODNNEFZ-BONVTDFDSA-N 0.000 claims 1
- LRMYUVNPSPTPOT-BONVTDFDSA-N (3S,4R)-4-(2,6-difluoro-4-methoxyphenyl)-3-[[5-[6-(trifluoromethyl)pyridin-3-yl]-1,3,4-thiadiazol-2-yl]amino]pyrrolidin-2-one Chemical compound COC1=CC(F)=C([C@H](CNC2=O)[C@@H]2NC2=NN=C(C3=CC=C(C(F)(F)F)N=C3)S2)C(F)=C1 LRMYUVNPSPTPOT-BONVTDFDSA-N 0.000 claims 1
- FRISEKWSFLYBKV-BONVTDFDSA-N (3S,4R)-4-(2,6-difluoro-4-methoxyphenyl)-3-[[5-[6-(trifluoromethylsulfanyl)pyridin-3-yl]-1,3,4-oxadiazol-2-yl]amino]pyrrolidin-2-one Chemical compound COC1=CC(F)=C([C@H](CNC2=O)[C@@H]2NC2=NN=C(C(C=N3)=CC=C3SC(F)(F)F)O2)C(F)=C1 FRISEKWSFLYBKV-BONVTDFDSA-N 0.000 claims 1
- JFOPMJDVYBMIIM-UWJYYQICSA-N 2-[4-[5-[[(3S,4R)-4-(2,6-difluoro-4-methoxyphenyl)-2-oxopyrrolidin-3-yl]amino]-1,3,4-oxadiazol-2-yl]phenoxy]pyridine-3-carbonitrile Chemical compound COC1=CC(F)=C([C@H](CNC2=O)[C@@H]2NC2=NN=C(C(C=C3)=CC=C3OC3=NC=CC=C3C#N)O2)C(F)=C1 JFOPMJDVYBMIIM-UWJYYQICSA-N 0.000 claims 1
- OOAHTWBNOVBNLD-JTSKRJEESA-N 2-[4-[5-[[(3S,4R)-4-(2,6-difluoro-4-methoxyphenyl)-2-oxopyrrolidin-3-yl]amino]-1,3,4-oxadiazol-2-yl]phenoxy]pyridine-4-carbonitrile Chemical compound COC1=CC(F)=C([C@H](CNC2=O)[C@@H]2NC2=NN=C(C(C=C3)=CC=C3OC3=NC=CC(C#N)=C3)O2)C(F)=C1 OOAHTWBNOVBNLD-JTSKRJEESA-N 0.000 claims 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- AZHKDQUHLHBGRM-CVDCTZTESA-N 4-[4-[5-[[(3S,4R)-4-(2,6-difluoro-4-methoxyphenyl)-2-oxopyrrolidin-3-yl]amino]-1,3,4-oxadiazol-2-yl]phenoxy]benzonitrile Chemical compound COC1=CC(F)=C([C@H](CNC2=O)[C@@H]2NC2=NN=C(C(C=C3)=CC=C3OC(C=C3)=CC=C3C#N)O2)C(F)=C1 AZHKDQUHLHBGRM-CVDCTZTESA-N 0.000 claims 1
- GEKVFUFYEIRIKT-GUYCJALGSA-N 4-[5-[[(3S,4R)-4-(2,6-difluoro-4-methoxyphenyl)-2-oxopyrrolidin-3-yl]amino]-1,3,4-oxadiazol-2-yl]benzonitrile Chemical compound COC1=CC(=C(C(=C1)F)[C@@H]2CNC(=O)[C@H]2NC3=NN=C(O3)C4=CC=C(C=C4)C#N)F GEKVFUFYEIRIKT-GUYCJALGSA-N 0.000 claims 1
- CUTPONSEEFDLLR-JTSKRJEESA-N 6-[4-[5-[[(3S,4R)-4-(2,6-difluoro-4-methoxyphenyl)-2-oxopyrrolidin-3-yl]amino]-1,3,4-oxadiazol-2-yl]phenoxy]pyridine-2-carbonitrile Chemical compound COC1=CC(F)=C([C@H](CNC2=O)[C@@H]2NC2=NN=C(C(C=C3)=CC=C3OC3=CC=CC(C#N)=N3)O2)C(F)=C1 CUTPONSEEFDLLR-JTSKRJEESA-N 0.000 claims 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/42—Oxazoles
- A61K31/423—Oxazoles condensed with carbocyclic rings
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
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- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4245—Oxadiazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/433—Thidiazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Cardiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
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- Epidemiology (AREA)
- Vascular Medicine (AREA)
- Hospice & Palliative Care (AREA)
- Urology & Nephrology (AREA)
- Pulmonology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Pyrrole Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201862771196P | 2018-11-26 | 2018-11-26 | |
| US201962819832P | 2019-03-18 | 2019-03-18 | |
| PCT/US2019/062905 WO2020112583A1 (en) | 2018-11-26 | 2019-11-25 | Pyrrolidinone derivatives as formyl peptide 2 receptor agonists |
Publications (1)
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|---|---|
| ES2964299T3 true ES2964299T3 (es) | 2024-04-05 |
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| ES19818484T Active ES2964299T3 (es) | 2018-11-26 | 2019-11-25 | Derivados de pirrolidinona como agonistas del receptor del péptido formilado 2 |
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| Country | Link |
|---|---|
| US (1) | US12281108B2 (https=) |
| EP (1) | EP3887366B1 (https=) |
| JP (1) | JP7398455B2 (https=) |
| KR (1) | KR102877973B1 (https=) |
| CN (1) | CN113166134B (https=) |
| ES (1) | ES2964299T3 (https=) |
| WO (1) | WO2020112583A1 (https=) |
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| CN116034104B (zh) * | 2020-07-09 | 2026-01-09 | 百时美施贵宝公司 | 氧代吡咯烷fpr2激动剂 |
| CA3185263A1 (en) | 2020-07-09 | 2022-01-13 | James A. Johnson | Pyrazolone formyl peptide 2 receptor agonists |
| KR20230051525A (ko) * | 2020-08-12 | 2023-04-18 | 브리스톨-마이어스 스큅 컴퍼니 | 옥소피롤리딘 우레아 fpr2 효능제 |
| ES2999626T3 (en) * | 2020-10-09 | 2025-02-26 | Bristol Myers Squibb Co | Aminoimidazole fpr2 agonists |
| EP4281452A4 (en) * | 2021-01-21 | 2024-11-06 | Beijing Tiantan Hospital | MODULATORS OF FPR1 AND METHODS OF USE THEREOF |
| WO2022155860A1 (en) * | 2021-01-21 | 2022-07-28 | Biofront Therapeutics (Beijing) Co., Ltd. | Modulators of fpr1 and methods of using the same |
| WO2022193187A1 (en) * | 2021-03-17 | 2022-09-22 | Biofront Ltd. (Cayman) | Modulators of fpr1 and methods of using same |
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| NZ720508A (en) * | 2013-11-28 | 2019-03-29 | Kyorin Seiyaku Kk | Urea derivative or pharmacologically acceptable salt thereof |
| WO2016189876A1 (en) | 2015-05-27 | 2016-12-01 | Kyorin Pharmaceutical Co., Ltd. | Urea derivative or pharmacologically acceptable salt thereof |
| JP6746614B2 (ja) | 2015-05-27 | 2020-08-26 | 杏林製薬株式会社 | ウレア誘導体、またはその薬理学的に許容される塩 |
| MX2018005756A (es) | 2015-11-24 | 2018-08-01 | Squibb Bristol Myers Co | Ubicacion como objetivo del receptor 2 de formilo-peptido/receptor de lipoxina a4 (fpr2/alx) para el tratamiento de enfermedades cardiacas. |
| JP6811241B2 (ja) | 2015-12-10 | 2021-01-13 | ブリストル−マイヤーズ スクイブ カンパニーＢｒｉｓｔｏｌ−Ｍｙｅｒｓ Ｓｑｕｉｂｂ Ｃｏｍｐａｎｙ | ピペリジノンホルミルペプチド受容体２およびホルミルペプチド受容体１アゴニスト |
| TW201815762A (zh) | 2016-09-21 | 2018-05-01 | 德商歌林達有限公司 | 經尿素及苯基取代之６員環狀胺或內醯胺 |
| JP2020015664A (ja) * | 2016-11-21 | 2020-01-30 | 宇部興産株式会社 | 含窒素多環式ヘテロ環誘導体 |
| WO2018213572A1 (en) * | 2017-05-17 | 2018-11-22 | William Marsh Rice University | Preparation of secondary amines with electrophilic n-linchpin reagents |
| KR102615099B1 (ko) | 2017-06-09 | 2023-12-15 | 브리스톨-마이어스 스큅 컴퍼니 | 아릴 헤테로시클릭 피페리디논 포르밀 펩티드 2 수용체 및 포르밀 펩티드 1 수용체 효능제 |
| EP3634958B1 (en) | 2017-06-09 | 2021-07-21 | Bristol-Myers Squibb Company | Cyclopropyl urea formyl peptide 2 receptor and formyl peptide 1 receptor agonists |
| KR102615095B1 (ko) | 2017-06-09 | 2023-12-15 | 브리스톨-마이어스 스큅 컴퍼니 | 피페리디논 포르밀 펩티드 2 수용체 효능제 |
| WO2018227065A1 (en) | 2017-06-09 | 2018-12-13 | Bristol-Myers Squibb Company | Piperidinone formyl peptide 2 receptor and formyl peptide 1 receptor agonists |
| KR102803660B1 (ko) | 2018-03-05 | 2025-05-02 | 브리스톨-마이어스 스큅 컴퍼니 | 페닐피롤리디논 포르밀 펩티드 2 수용체 효능제 |
| EP3986903B1 (en) | 2019-06-18 | 2023-05-10 | Bristol-Myers Squibb Company | Biaryl dialkyl phosphine oxide fpr2 agonists |
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2019
- 2019-11-25 CN CN201980077329.9A patent/CN113166134B/zh active Active
- 2019-11-25 US US17/295,092 patent/US12281108B2/en active Active
- 2019-11-25 WO PCT/US2019/062905 patent/WO2020112583A1/en not_active Ceased
- 2019-11-25 KR KR1020217019403A patent/KR102877973B1/ko active Active
- 2019-11-25 ES ES19818484T patent/ES2964299T3/es active Active
- 2019-11-25 EP EP19818484.8A patent/EP3887366B1/en active Active
- 2019-11-25 JP JP2021529452A patent/JP7398455B2/ja active Active
Also Published As
| Publication number | Publication date |
|---|---|
| EP3887366B1 (en) | 2023-09-27 |
| CN113166134A (zh) | 2021-07-23 |
| EP3887366A1 (en) | 2021-10-06 |
| US12281108B2 (en) | 2025-04-22 |
| US20220002281A1 (en) | 2022-01-06 |
| JP7398455B2 (ja) | 2023-12-14 |
| CN113166134B (zh) | 2024-06-14 |
| WO2020112583A1 (en) | 2020-06-04 |
| KR102877973B1 (ko) | 2025-10-30 |
| JP2022508218A (ja) | 2022-01-19 |
| KR20210095897A (ko) | 2021-08-03 |
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