MXPA05002066A - 2,5-dioxoimidazolidin-4-il acetamidas y analogos como inhibidores de la metaloproteinasa mmp12. - Google Patents
2,5-dioxoimidazolidin-4-il acetamidas y analogos como inhibidores de la metaloproteinasa mmp12.Info
- Publication number
- MXPA05002066A MXPA05002066A MXPA05002066A MXPA05002066A MXPA05002066A MX PA05002066 A MXPA05002066 A MX PA05002066A MX PA05002066 A MXPA05002066 A MX PA05002066A MX PA05002066 A MXPA05002066 A MX PA05002066A MX PA05002066 A MXPA05002066 A MX PA05002066A
- Authority
- MX
- Mexico
- Prior art keywords
- acetamide
- dioxoimidazolidin
- ethyl
- methyl
- phenyl
- Prior art date
Links
- 239000003112 inhibitor Substances 0.000 title abstract description 9
- 102000005741 Metalloproteases Human genes 0.000 title description 10
- 108010006035 Metalloproteases Proteins 0.000 title description 10
- CSGWGMMFAMMBSX-UHFFFAOYSA-N n-(2,5-dioxoimidazolidin-4-yl)acetamide Chemical class CC(=O)NC1NC(=O)NC1=O CSGWGMMFAMMBSX-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 82
- 238000000034 method Methods 0.000 claims abstract description 30
- 238000002360 preparation method Methods 0.000 claims abstract description 12
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 11
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims abstract description 10
- 238000002560 therapeutic procedure Methods 0.000 claims abstract description 6
- 238000011282 treatment Methods 0.000 claims abstract description 6
- 208000006673 asthma Diseases 0.000 claims abstract description 5
- 101000577881 Homo sapiens Macrophage metalloelastase Proteins 0.000 claims abstract description 3
- 238000004519 manufacturing process Methods 0.000 claims abstract description 3
- -1 cyano, carboxyl Chemical group 0.000 claims description 268
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 59
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 57
- 125000001424 substituent group Chemical group 0.000 claims description 57
- 125000004122 cyclic group Chemical group 0.000 claims description 45
- 229910052736 halogen Inorganic materials 0.000 claims description 43
- 150000002367 halogens Chemical class 0.000 claims description 43
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 40
- 125000000217 alkyl group Chemical group 0.000 claims description 37
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 37
- 229910052717 sulfur Inorganic materials 0.000 claims description 35
- 125000005842 heteroatom Chemical group 0.000 claims description 34
- 229910052739 hydrogen Inorganic materials 0.000 claims description 34
- 229910052760 oxygen Inorganic materials 0.000 claims description 33
- 239000001257 hydrogen Substances 0.000 claims description 32
- 150000003839 salts Chemical class 0.000 claims description 32
- 229910052757 nitrogen Inorganic materials 0.000 claims description 29
- 239000001301 oxygen Substances 0.000 claims description 29
- 229920006395 saturated elastomer Polymers 0.000 claims description 29
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 28
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 28
- 239000011593 sulfur Substances 0.000 claims description 28
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 27
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 24
- 239000012453 solvate Substances 0.000 claims description 24
- 125000003545 alkoxy group Chemical group 0.000 claims description 21
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 21
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 19
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 18
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 15
- 201000010099 disease Diseases 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 125000005843 halogen group Chemical group 0.000 claims description 13
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 13
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 12
- 125000001544 thienyl group Chemical group 0.000 claims description 12
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 11
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 11
- 125000004076 pyridyl group Chemical group 0.000 claims description 11
- 125000002541 furyl group Chemical group 0.000 claims description 10
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 10
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 9
- 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 claims description 9
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 9
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 125000001624 naphthyl group Chemical group 0.000 claims description 9
- 125000000449 nitro group Chemical class [O-][N+](*)=O 0.000 claims description 9
- 125000003386 piperidinyl group Chemical group 0.000 claims description 9
- 125000002947 alkylene group Chemical group 0.000 claims description 8
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 8
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 8
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 8
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 7
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 7
- 125000002883 imidazolyl group Chemical group 0.000 claims description 7
- 125000001041 indolyl group Chemical group 0.000 claims description 7
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 7
- 125000000335 thiazolyl group Chemical group 0.000 claims description 7
- 239000002671 adjuvant Substances 0.000 claims description 6
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 6
- 239000003085 diluting agent Substances 0.000 claims description 6
- 125000000842 isoxazolyl group Chemical group 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
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 6
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 6
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 6
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 6
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 6
- 125000001984 thiazolidinyl group Chemical group 0.000 claims description 6
- 125000001425 triazolyl group Chemical group 0.000 claims description 6
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 5
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims description 5
- 125000001188 haloalkyl group Chemical group 0.000 claims description 5
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 5
- 125000002757 morpholinyl group Chemical group 0.000 claims description 5
- IORHYLHMWHRAJN-UHFFFAOYSA-N 2-(2,5-dioxoimidazolidin-4-yl)-n-[2-[4-(2-phenylethynyl)piperidin-1-yl]ethyl]acetamide Chemical compound C1CC(C#CC=2C=CC=CC=2)CCN1CCNC(=O)CC1NC(=O)NC1=O IORHYLHMWHRAJN-UHFFFAOYSA-N 0.000 claims description 4
- OILZRECTMVSBKC-UHFFFAOYSA-N 2-(2,5-dioxoimidazolidin-4-yl)-n-[2-[4-[4-(trifluoromethyl)phenoxy]phenyl]ethyl]acetamide Chemical compound C1=CC(C(F)(F)F)=CC=C1OC(C=C1)=CC=C1CCNC(=O)CC1C(=O)NC(=O)N1 OILZRECTMVSBKC-UHFFFAOYSA-N 0.000 claims description 4
- NJMHVZCQFIPWHL-UHFFFAOYSA-N 2-(2,5-dioxoimidazolidin-4-yl)-n-methyl-n-[2-(4-phenylphenyl)ethyl]acetamide Chemical compound N1C(=O)NC(=O)C1CC(=O)N(C)CCC(C=C1)=CC=C1C1=CC=CC=C1 NJMHVZCQFIPWHL-UHFFFAOYSA-N 0.000 claims description 4
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 4
- 102100027998 Macrophage metalloelastase Human genes 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 4
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 125000004981 cycloalkylmethyl group Chemical group 0.000 claims description 4
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 claims description 4
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 4
- 230000000414 obstructive effect Effects 0.000 claims description 4
- 125000004043 oxo group Chemical group O=* 0.000 claims description 4
- 125000004193 piperazinyl group Chemical group 0.000 claims description 4
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 4
- SIEGPBNPMLNAIX-UHFFFAOYSA-N 2-(2,5-dioxoimidazolidin-4-yl)-n-(1-hydroxy-1-phenylpropan-2-yl)acetamide Chemical compound C=1C=CC=CC=1C(O)C(C)NC(=O)CC1NC(=O)NC1=O SIEGPBNPMLNAIX-UHFFFAOYSA-N 0.000 claims description 3
- VWFHRFVESALJFX-UHFFFAOYSA-N 2-(2,5-dioxoimidazolidin-4-yl)-n-(2-phenylcyclopropyl)acetamide Chemical compound C1C(C=2C=CC=CC=2)C1NC(=O)CC1NC(=O)NC1=O VWFHRFVESALJFX-UHFFFAOYSA-N 0.000 claims description 3
- XIWREPKZTFSDQK-UHFFFAOYSA-N 2-(2,5-dioxoimidazolidin-4-yl)-n-[2-(4-fluorophenyl)ethyl]acetamide Chemical compound C1=CC(F)=CC=C1CCNC(=O)CC1C(=O)NC(=O)N1 XIWREPKZTFSDQK-UHFFFAOYSA-N 0.000 claims description 3
- QOUUSQCTLZIPHV-UHFFFAOYSA-N 2-(2,5-dioxoimidazolidin-4-yl)-n-[2-(4-phenoxyphenyl)ethyl]acetamide Chemical compound C=1C=C(OC=2C=CC=CC=2)C=CC=1CCNC(=O)CC1NC(=O)NC1=O QOUUSQCTLZIPHV-UHFFFAOYSA-N 0.000 claims description 3
- KJDLMPRNRVVGBT-UHFFFAOYSA-N 2-(2,5-dioxoimidazolidin-4-yl)-n-[2-(4-pyridin-3-ylphenyl)ethyl]acetamide Chemical compound C=1C=C(C=2C=NC=CC=2)C=CC=1CCNC(=O)CC1NC(=O)NC1=O KJDLMPRNRVVGBT-UHFFFAOYSA-N 0.000 claims description 3
- QXYKUMMYJROWDF-UHFFFAOYSA-N 2-(2,5-dioxoimidazolidin-4-yl)-n-[2-(4-quinolin-3-ylphenyl)propyl]acetamide Chemical compound C=1C=C(C=2C=C3C=CC=CC3=NC=2)C=CC=1C(C)CNC(=O)CC1NC(=O)NC1=O QXYKUMMYJROWDF-UHFFFAOYSA-N 0.000 claims description 3
- KXFQGBOGUBMENC-UHFFFAOYSA-N 2-(2,5-dioxoimidazolidin-4-yl)-n-[2-[4-(4-methoxy-3-methylphenyl)phenyl]propyl]acetamide Chemical compound C1=C(C)C(OC)=CC=C1C1=CC=C(C(C)CNC(=O)CC2C(NC(=O)N2)=O)C=C1 KXFQGBOGUBMENC-UHFFFAOYSA-N 0.000 claims description 3
- ZCBKHMMOOUJAGQ-UHFFFAOYSA-N 2-(2,5-dioxoimidazolidin-4-yl)-n-[2-[4-(furan-2-yl)phenyl]ethyl]acetamide Chemical compound C=1C=C(C=2OC=CC=2)C=CC=1CCNC(=O)CC1NC(=O)NC1=O ZCBKHMMOOUJAGQ-UHFFFAOYSA-N 0.000 claims description 3
- QIBNWYVDFQPFTQ-UHFFFAOYSA-N 2-(2,5-dioxoimidazolidin-4-yl)-n-[2-methoxy-2-(4-phenylphenyl)ethyl]acetamide Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1C(OC)CNC(=O)CC1NC(=O)NC1=O QIBNWYVDFQPFTQ-UHFFFAOYSA-N 0.000 claims description 3
- IQBJRZKOGWOTGY-MDECGGOYSA-N 2-[(1S,2R)-2-[4-(4-acetamidophenyl)phenyl]cyclopropyl]-2-(4-methyl-2,5-dioxoimidazolidin-4-yl)acetamide Chemical compound C(C)(=O)NC1=CC=C(C=C1)C1=CC=C(C=C1)[C@H]1[C@H](C1)C(C(=O)N)C1(NC(NC1=O)=O)C IQBJRZKOGWOTGY-MDECGGOYSA-N 0.000 claims description 3
- HAIMDPFUZXDPMO-UHFFFAOYSA-N 2-[5-(3-acetamidophenyl)-2,3-dihydro-1H-inden-2-yl]-2-(2,5-dioxoimidazolidin-4-yl)acetamide Chemical compound C(C)(=O)NC=1C=C(C=CC=1)C=1C=C2CC(CC2=CC=1)C(C(=O)N)C1NC(NC1=O)=O HAIMDPFUZXDPMO-UHFFFAOYSA-N 0.000 claims description 3
- IALKQEMNHZYJMA-UHFFFAOYSA-N 4-[4-(1-benzothiophen-2-yl)phenyl]-2-(2,5-dioxoimidazolidin-4-yl)pentanamide Chemical compound C=1C=C(C=2SC3=CC=CC=C3C=2)C=CC=1C(C)CC(C(N)=O)C1NC(=O)NC1=O IALKQEMNHZYJMA-UHFFFAOYSA-N 0.000 claims description 3
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- 230000001404 mediated effect Effects 0.000 claims description 3
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 3
- WNKPUBQSOKZDEN-HVHHGIHYSA-N n-[(1s,2r)-2-[4-(4-cyanophenyl)phenyl]cyclopropyl]-2-(4-methyl-2,5-dioxoimidazolidin-4-yl)acetamide Chemical compound N([C@@H]1[C@H](C1)C=1C=CC(=CC=1)C=1C=CC(=CC=1)C#N)C(=O)CC1(C)NC(=O)NC1=O WNKPUBQSOKZDEN-HVHHGIHYSA-N 0.000 claims description 3
- QWCLEQZHLRHDAN-UHFFFAOYSA-N n-[1-(4-chlorophenyl)ethyl]-2-(2,5-dioxoimidazolidin-4-yl)acetamide Chemical compound C=1C=C(Cl)C=CC=1C(C)NC(=O)CC1NC(=O)NC1=O QWCLEQZHLRHDAN-UHFFFAOYSA-N 0.000 claims description 3
- PVEQMXNETCVAMN-UHFFFAOYSA-N n-[2-(4-chlorophenyl)ethyl]-2-(2,5-dioxoimidazolidin-4-yl)acetamide Chemical compound C1=CC(Cl)=CC=C1CCNC(=O)CC1C(=O)NC(=O)N1 PVEQMXNETCVAMN-UHFFFAOYSA-N 0.000 claims description 3
- JZEWPZXQMPMYFA-UHFFFAOYSA-N n-[2-[4-(3-acetylphenyl)phenyl]propyl]-2-(2,5-dioxoimidazolidin-4-yl)acetamide Chemical compound C=1C=C(C=2C=C(C=CC=2)C(C)=O)C=CC=1C(C)CNC(=O)CC1NC(=O)NC1=O JZEWPZXQMPMYFA-UHFFFAOYSA-N 0.000 claims description 3
- ROWFBHSRTNSLLQ-UHFFFAOYSA-N n-[2-[4-(4-cyanophenyl)phenyl]propyl]-2-(4-methyl-2,5-dioxoimidazolidin-4-yl)acetamide Chemical compound C=1C=C(C=2C=CC(=CC=2)C#N)C=CC=1C(C)CNC(=O)CC1(C)NC(=O)NC1=O ROWFBHSRTNSLLQ-UHFFFAOYSA-N 0.000 claims description 3
- HISFYRVDPDIRGA-UHFFFAOYSA-N n-[5-(1-benzothiophen-2-yl)-2,3-dihydro-1h-inden-2-yl]-2-(2,5-dioxoimidazolidin-4-yl)acetamide Chemical compound C1C2=CC=C(C=3SC4=CC=CC=C4C=3)C=C2CC1NC(=O)CC1NC(=O)NC1=O HISFYRVDPDIRGA-UHFFFAOYSA-N 0.000 claims description 3
- ATRCLXVWBGMAMK-UHFFFAOYSA-N n-[5-(3-acetylphenyl)-2,3-dihydro-1h-inden-2-yl]-2-(4-methyl-2,5-dioxoimidazolidin-4-yl)acetamide Chemical compound CC(=O)C1=CC=CC(C=2C=C3CC(CC3=CC=2)NC(=O)CC2(C)C(NC(=O)N2)=O)=C1 ATRCLXVWBGMAMK-UHFFFAOYSA-N 0.000 claims description 3
- JHFGZSMXRADXDZ-UHFFFAOYSA-N n-[5-(3-cyanophenyl)-2,3-dihydro-1h-inden-2-yl]-2-(4-methyl-2,5-dioxoimidazolidin-4-yl)acetamide Chemical compound C1C2=CC=C(C=3C=C(C=CC=3)C#N)C=C2CC1NC(=O)CC1(C)NC(=O)NC1=O JHFGZSMXRADXDZ-UHFFFAOYSA-N 0.000 claims description 3
- ZWXTZQFWZCVQHZ-UHFFFAOYSA-N n-[5-(3-methoxyphenyl)-2,3-dihydro-1h-inden-2-yl]-2-(4-methyl-2,5-dioxoimidazolidin-4-yl)acetamide Chemical compound COC1=CC=CC(C=2C=C3CC(CC3=CC=2)NC(=O)CC2(C)C(NC(=O)N2)=O)=C1 ZWXTZQFWZCVQHZ-UHFFFAOYSA-N 0.000 claims description 3
- PFRGJXSNDNBKHU-UHFFFAOYSA-N n-[5-(4-acetylphenyl)-2,3-dihydro-1h-inden-2-yl]-2-(2,5-dioxoimidazolidin-4-yl)acetamide Chemical compound C1=CC(C(=O)C)=CC=C1C1=CC=C(CC(C2)NC(=O)CC3C(NC(=O)N3)=O)C2=C1 PFRGJXSNDNBKHU-UHFFFAOYSA-N 0.000 claims description 3
- WSPQEPKTKYUGGH-UHFFFAOYSA-N n-[5-(4-acetylphenyl)-2,3-dihydro-1h-inden-2-yl]-2-(4-methyl-2,5-dioxoimidazolidin-4-yl)acetamide Chemical compound C1=CC(C(=O)C)=CC=C1C1=CC=C(CC(C2)NC(=O)CC3(C)C(NC(=O)N3)=O)C2=C1 WSPQEPKTKYUGGH-UHFFFAOYSA-N 0.000 claims description 3
- 208000023504 respiratory system disease Diseases 0.000 claims description 3
- SMLVTOYIPFGBCQ-UHFFFAOYSA-N 2-(2,5-dioxoimidazolidin-4-yl)-n-[2-(7-methyl-1h-indol-3-yl)ethyl]acetamide Chemical compound C=1NC=2C(C)=CC=CC=2C=1CCNC(=O)CC1NC(=O)NC1=O SMLVTOYIPFGBCQ-UHFFFAOYSA-N 0.000 claims description 2
- KVCRCZGTISUDIT-UHFFFAOYSA-N 2-(2,5-dioxoimidazolidin-4-yl)-n-[2-[4-(3-nitrophenyl)phenyl]ethyl]acetamide Chemical compound [O-][N+](=O)C1=CC=CC(C=2C=CC(CCNC(=O)CC3C(NC(=O)N3)=O)=CC=2)=C1 KVCRCZGTISUDIT-UHFFFAOYSA-N 0.000 claims description 2
- JRSVKPOMJWSJBK-UHFFFAOYSA-N 2-(2,5-dioxoimidazolidin-4-yl)-n-[2-[4-(4-fluorophenyl)phenyl]propyl]acetamide Chemical compound C=1C=C(C=2C=CC(F)=CC=2)C=CC=1C(C)CNC(=O)CC1NC(=O)NC1=O JRSVKPOMJWSJBK-UHFFFAOYSA-N 0.000 claims description 2
- OAOVFHJGNLNRAT-UHFFFAOYSA-N 2-(2,5-dioxoimidazolidin-4-yl)-n-[5-(4-fluoro-3-methylphenyl)-2,3-dihydro-1h-inden-2-yl]acetamide Chemical compound C1=C(F)C(C)=CC(C=2C=C3CC(CC3=CC=2)NC(=O)CC2C(NC(=O)N2)=O)=C1 OAOVFHJGNLNRAT-UHFFFAOYSA-N 0.000 claims description 2
- XOWIGLBFFHBXIC-UHFFFAOYSA-N 2-(4-methyl-2,5-dioxoimidazolidin-4-yl)-n-[2-[4-[3-(trifluoromethoxy)phenyl]phenyl]propyl]acetamide Chemical compound C=1C=C(C=2C=C(OC(F)(F)F)C=CC=2)C=CC=1C(C)CNC(=O)CC1(C)NC(=O)NC1=O XOWIGLBFFHBXIC-UHFFFAOYSA-N 0.000 claims description 2
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 2
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
- KRKPYFLIYNGWTE-UHFFFAOYSA-N n,o-dimethylhydroxylamine Chemical compound CNOC KRKPYFLIYNGWTE-UHFFFAOYSA-N 0.000 claims description 2
- IQSZYCFOEIIHFK-BEWYTNLXSA-N n-[(1s,2r)-2-[4-(4-acetylphenyl)phenyl]cyclopropyl]-2-(4-methyl-2,5-dioxoimidazolidin-4-yl)acetamide Chemical compound C1=CC(C(=O)C)=CC=C1C1=CC=C([C@@H]2[C@H](C2)NC(=O)CC2(C)C(NC(=O)N2)=O)C=C1 IQSZYCFOEIIHFK-BEWYTNLXSA-N 0.000 claims description 2
- PHYJBVTUWHGPIP-UHFFFAOYSA-N n-[2-(4-chlorophenyl)propyl]-2-(4-methyl-2,5-dioxoimidazolidin-4-yl)acetamide Chemical compound C=1C=C(Cl)C=CC=1C(C)CNC(=O)CC1(C)NC(=O)NC1=O PHYJBVTUWHGPIP-UHFFFAOYSA-N 0.000 claims description 2
- SCWMECAYLFDSKL-UHFFFAOYSA-N n-[2-[4-(1-benzofuran-2-yl)phenyl]ethyl]-2-(2,5-dioxoimidazolidin-4-yl)acetamide Chemical compound C=1C=C(C=2OC3=CC=CC=C3C=2)C=CC=1CCNC(=O)CC1NC(=O)NC1=O SCWMECAYLFDSKL-UHFFFAOYSA-N 0.000 claims description 2
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- LIGACIXOYTUXAW-UHFFFAOYSA-N phenacyl bromide Chemical compound BrCC(=O)C1=CC=CC=C1 LIGACIXOYTUXAW-UHFFFAOYSA-N 0.000 description 1
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- XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
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- 229910000104 sodium hydride Inorganic materials 0.000 description 1
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- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
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- GPTXCAZYUMDUMN-UHFFFAOYSA-N tert-butyl n-(2-hydroxyethyl)carbamate Chemical compound CC(C)(C)OC(=O)NCCO GPTXCAZYUMDUMN-UHFFFAOYSA-N 0.000 description 1
- LALFAEKVNOWOKJ-UHFFFAOYSA-N tert-butyl n-[2-[4-(4-fluorophenyl)phenyl]propyl]carbamate Chemical compound C1=CC(C(CNC(=O)OC(C)(C)C)C)=CC=C1C1=CC=C(F)C=C1 LALFAEKVNOWOKJ-UHFFFAOYSA-N 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C07—ORGANIC CHEMISTRY
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- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
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Landscapes
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| SE0202539A SE0202539D0 (sv) | 2002-08-27 | 2002-08-27 | Compounds |
| PCT/SE2003/001328 WO2004020415A1 (en) | 2002-08-27 | 2003-08-26 | 2,5-dioxoimidazolidin-4-yl acetamides and analogues as inhibitors of metalloproteinase mmp12. |
Publications (1)
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| MXPA05002066A true MXPA05002066A (es) | 2005-06-08 |
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| ITRE20010042A1 (it) * | 2001-04-24 | 2002-10-24 | Corghi Spa | Dispositivo sollevatore per macchine smontagomme |
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| US7321065B2 (en) | 2003-04-18 | 2008-01-22 | The Regents Of The University Of California | Thyronamine derivatives and analogs and methods of use thereof |
| US6979750B1 (en) | 2003-04-18 | 2005-12-27 | The Regents Of The University Of California | Thyronamine derivatives and analogs and methods of use thereof |
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| SE0401762D0 (sv) | 2004-07-05 | 2004-07-05 | Astrazeneca Ab | Novel compounds |
| ATE508744T1 (de) * | 2004-08-19 | 2011-05-15 | Quest Pharmaceutical Services | 5-ä3-(4-benzyloxyphenylthio)-fur-2-ylü- imidazolidin-2, 4-dion und analoga als hemmer der makrophagenelastase |
| SE0403085D0 (sv) * | 2004-12-17 | 2004-12-17 | Astrazeneca Ab | Novel componds |
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| EP2096107A1 (en) | 2004-12-23 | 2009-09-02 | GPC Biotech AG | Derivatives of squaric acid with anti-proliferative activity |
| EP1859356B1 (en) * | 2005-03-16 | 2019-07-10 | Sensus Metering Systems Inc. | Method, system, apparatus, and computer program product for determining a physical location of a sensor |
| WO2008051260A1 (en) * | 2006-01-13 | 2008-05-02 | Battelle Memorial Institute | Methods for assessing copd-retlated diseases |
| TW200740769A (en) * | 2006-03-16 | 2007-11-01 | Astrazeneca Ab | Novel process |
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| TW200831488A (en) * | 2006-11-29 | 2008-08-01 | Astrazeneca Ab | Novel compounds |
| CN101024619B (zh) * | 2007-03-29 | 2010-12-01 | 上海大学 | N-取代邻溴苄酰胺的合成方法 |
| WO2010003624A2 (en) | 2008-07-09 | 2010-01-14 | Sanofi-Aventis | Heterocyclic compounds, processes for their preparation, medicaments comprising these compounds, and the use thereof |
| EP2361242B1 (en) | 2008-10-17 | 2018-08-01 | Oryzon Genomics, S.A. | Oxidase inhibitors and their use |
| WO2010084160A1 (en) | 2009-01-21 | 2010-07-29 | Oryzon Genomics S.A. | Phenylcyclopropylamine derivatives and their medical use |
| FR2944525B1 (fr) * | 2009-04-17 | 2011-06-24 | Ipsen Pharma Sas | Derives d'imidazolidine-2,4-dione et leur utilisation comme medicament |
| CA2812683C (en) | 2009-09-25 | 2017-10-10 | Oryzon Genomics S.A. | Lysine specific demethylase-1 inhibitors and their use |
| US8946296B2 (en) | 2009-10-09 | 2015-02-03 | Oryzon Genomics S.A. | Substituted heteroaryl- and aryl-cyclopropylamine acetamides and their use |
| WO2011106105A2 (en) | 2010-02-24 | 2011-09-01 | Oryzon Genomics, S.A. | Inhibitors for antiviral use |
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| HUE030938T2 (en) | 2010-04-19 | 2017-06-28 | Oryzon Genomics Sa | Lysine-specific demethylase-1 inhibitors and their use |
| MX341732B (es) | 2010-07-29 | 2016-08-30 | Oryzon Genomics S A * | Inhibidores de la demetilasa lsd1 basados en arilciclopropilamina y sus usos médicos. |
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| EP2741741A2 (en) * | 2011-05-19 | 2014-06-18 | Oryzon Genomics, S.A. | Lysine demethylase inhibitors for inflammatory diseases or conditions |
| BR112014009306B1 (pt) | 2011-10-20 | 2021-07-20 | Oryzon Genomics S.A. | Compostos de (hetero)aril ciclopropilamina como inibidores de lsd1 |
| WO2013057322A1 (en) | 2011-10-20 | 2013-04-25 | Oryzon Genomics, S.A. | (hetero)aryl cyclopropylamine compounds as lsd1 inhibitors |
| US9023146B2 (en) | 2012-09-25 | 2015-05-05 | Empire Technology Development Llc | Oxidizing agents on pigments |
| AR092971A1 (es) * | 2012-10-26 | 2015-05-06 | Lilly Co Eli | Inhibidores de agrecanasa |
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