AU3821502A - Method of treating or inhibiting neutrophil chemotaxis by administering a mek inhibitor - Google Patents
Method of treating or inhibiting neutrophil chemotaxis by administering a mek inhibitor Download PDFInfo
- Publication number
- AU3821502A AU3821502A AU38215/02A AU3821502A AU3821502A AU 3821502 A AU3821502 A AU 3821502A AU 38215/02 A AU38215/02 A AU 38215/02A AU 3821502 A AU3821502 A AU 3821502A AU 3821502 A AU3821502 A AU 3821502A
- Authority
- AU
- Australia
- Prior art keywords
- benzamide
- phenylamino
- iodo
- difluoro
- methyl
- 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.)
- Abandoned
Links
- 238000000034 method Methods 0.000 title claims description 54
- 239000002829 mitogen activated protein kinase inhibitor Substances 0.000 title claims description 49
- 229940124647 MEK inhibitor Drugs 0.000 title claims description 47
- 230000002401 inhibitory effect Effects 0.000 title claims description 13
- 230000011242 neutrophil chemotaxis Effects 0.000 title description 14
- -1 2 -chloro- 4 -iodo-phenylamino Chemical group 0.000 claims description 182
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 158
- 125000000217 alkyl group Chemical group 0.000 claims description 88
- 150000001875 compounds Chemical class 0.000 claims description 84
- 210000000440 neutrophil Anatomy 0.000 claims description 65
- 229910052739 hydrogen Inorganic materials 0.000 claims description 48
- 239000001257 hydrogen Substances 0.000 claims description 46
- QDLHCMPXEPAAMD-QAIWCSMKSA-N wortmannin Chemical compound C1([C@]2(C)C3=C(C4=O)OC=C3C(=O)O[C@@H]2COC)=C4[C@@H]2CCC(=O)[C@@]2(C)C[C@H]1OC(C)=O QDLHCMPXEPAAMD-QAIWCSMKSA-N 0.000 claims description 42
- QDLHCMPXEPAAMD-UHFFFAOYSA-N wortmannin Natural products COCC1OC(=O)C2=COC(C3=O)=C2C1(C)C1=C3C2CCC(=O)C2(C)CC1OC(C)=O QDLHCMPXEPAAMD-UHFFFAOYSA-N 0.000 claims description 42
- GFMMXOIFOQCCGU-UHFFFAOYSA-N 2-(2-chloro-4-iodoanilino)-N-(cyclopropylmethoxy)-3,4-difluorobenzamide Chemical compound C=1C=C(I)C=C(Cl)C=1NC1=C(F)C(F)=CC=C1C(=O)NOCC1CC1 GFMMXOIFOQCCGU-UHFFFAOYSA-N 0.000 claims description 36
- 125000003545 alkoxy group Chemical group 0.000 claims description 34
- 150000002431 hydrogen Chemical class 0.000 claims description 31
- 230000005012 migration Effects 0.000 claims description 31
- 238000013508 migration Methods 0.000 claims description 31
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 23
- 230000005764 inhibitory process Effects 0.000 claims description 22
- 125000003118 aryl group Chemical group 0.000 claims description 20
- 229940043441 phosphoinositide 3-kinase inhibitor Drugs 0.000 claims description 20
- 239000012828 PI3K inhibitor Substances 0.000 claims description 19
- 125000001072 heteroaryl group Chemical group 0.000 claims description 19
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 17
- 125000005843 halogen group Chemical group 0.000 claims description 17
- 150000003839 salts Chemical class 0.000 claims description 17
- 239000005711 Benzoic acid Substances 0.000 claims description 16
- 229910052794 bromium Inorganic materials 0.000 claims description 16
- 125000005842 heteroatom Chemical group 0.000 claims description 16
- 201000010099 disease Diseases 0.000 claims description 15
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
- 150000002148 esters Chemical class 0.000 claims description 14
- 229910052717 sulfur Inorganic materials 0.000 claims description 14
- 150000001408 amides Chemical class 0.000 claims description 13
- 125000003342 alkenyl group Chemical group 0.000 claims description 12
- 125000004104 aryloxy group Chemical group 0.000 claims description 12
- 125000004122 cyclic group Chemical group 0.000 claims description 12
- 125000000304 alkynyl group Chemical group 0.000 claims description 11
- 229910052740 iodine Inorganic materials 0.000 claims description 11
- 230000001404 mediated effect Effects 0.000 claims description 11
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
- 229910052731 fluorine Inorganic materials 0.000 claims description 9
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 8
- 239000011737 fluorine Substances 0.000 claims description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 229940002612 prodrug Drugs 0.000 claims description 8
- 239000000651 prodrug Substances 0.000 claims description 8
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 125000003282 alkyl amino group Chemical group 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- 239000000460 chlorine Substances 0.000 claims description 5
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 4
- GUAFZVVAOQFCPJ-UHFFFAOYSA-N 5-bromo-n-(2-hydroxyethyl)-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC=C(Br)C=C1C(=O)NCCO GUAFZVVAOQFCPJ-UHFFFAOYSA-N 0.000 claims description 4
- DMXADGCWZHCXBU-UHFFFAOYSA-N 5-chloro-n-(2-hydroxyethyl)-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC=C(Cl)C=C1C(=O)NCCO DMXADGCWZHCXBU-UHFFFAOYSA-N 0.000 claims description 4
- 201000003883 Cystic fibrosis Diseases 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
- SUDAHWBOROXANE-SECBINFHSA-N PD 0325901 Chemical compound OC[C@@H](O)CONC(=O)C1=CC=C(F)C(F)=C1NC1=CC=C(I)C=C1F SUDAHWBOROXANE-SECBINFHSA-N 0.000 claims description 4
- 230000001154 acute effect Effects 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- XKRVQEHFHLIYHN-UHFFFAOYSA-N 2-(4-iodo-2-methylanilino)-n-methyl-5-nitro-n-phenylbenzamide Chemical compound C=1C=CC=CC=1N(C)C(=O)C1=CC([N+]([O-])=O)=CC=C1NC1=CC=C(I)C=C1C XKRVQEHFHLIYHN-UHFFFAOYSA-N 0.000 claims description 3
- YZVHIDUDGXLOLY-UHFFFAOYSA-N 5-bromo-2-(2-chloro-4-iodoanilino)-3,4-difluoro-n-(3-hydroxypropoxy)benzamide Chemical compound OCCCONC(=O)C1=CC(Br)=C(F)C(F)=C1NC1=CC=C(I)C=C1Cl YZVHIDUDGXLOLY-UHFFFAOYSA-N 0.000 claims description 3
- AANZSIPSXXHMRM-UHFFFAOYSA-N 5-bromo-2-(4-iodo-2-methylanilino)-n-phenylmethoxybenzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC=C(Br)C=C1C(=O)NOCC1=CC=CC=C1 AANZSIPSXXHMRM-UHFFFAOYSA-N 0.000 claims description 3
- ASLGKYRJGJLPAE-UHFFFAOYSA-N 5-chloro-2-(2-chloro-4-iodoanilino)-n-(2,3-dihydroxypropoxy)-3,4-difluorobenzamide Chemical compound OCC(O)CONC(=O)C1=CC(Cl)=C(F)C(F)=C1NC1=CC=C(I)C=C1Cl ASLGKYRJGJLPAE-UHFFFAOYSA-N 0.000 claims description 3
- MFISPQKUQORGHB-UHFFFAOYSA-N 5-chloro-2-(4-iodo-2-methylanilino)-n-methyl-n-phenylbenzamide Chemical compound C=1C=CC=CC=1N(C)C(=O)C1=CC(Cl)=CC=C1NC1=CC=C(I)C=C1C MFISPQKUQORGHB-UHFFFAOYSA-N 0.000 claims description 3
- NRQYGGWYEHEXEJ-UHFFFAOYSA-N 5-chloro-n-cyclopropyl-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC=C(Cl)C=C1C(=O)NC1CC1 NRQYGGWYEHEXEJ-UHFFFAOYSA-N 0.000 claims description 3
- PJCPYFYKAWDPLX-UHFFFAOYSA-N 5-fluoro-2-(4-iodo-2-methylanilino)-n-[(4-sulfamoylphenyl)methyl]benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC=C(F)C=C1C(=O)NCC1=CC=C(S(N)(=O)=O)C=C1 PJCPYFYKAWDPLX-UHFFFAOYSA-N 0.000 claims description 3
- KCOUCDQMKMTOGV-UHFFFAOYSA-N 5-fluoro-2-(4-iodo-2-methylanilino)-n-methyl-n-phenylbenzamide Chemical compound C=1C=CC=CC=1N(C)C(=O)C1=CC(F)=CC=C1NC1=CC=C(I)C=C1C KCOUCDQMKMTOGV-UHFFFAOYSA-N 0.000 claims description 3
- CCGNHTHRIVEZPG-UHFFFAOYSA-N 5-fluoro-2-(4-iodo-2-methylanilino)-n-phenylmethoxybenzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC=C(F)C=C1C(=O)NOCC1=CC=CC=C1 CCGNHTHRIVEZPG-UHFFFAOYSA-N 0.000 claims description 3
- CLOSFYSFDCNULT-UHFFFAOYSA-N 5-iodo-2-(4-iodo-2-methylanilino)-n-phenylmethoxybenzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC=C(I)C=C1C(=O)NOCC1=CC=CC=C1 CLOSFYSFDCNULT-UHFFFAOYSA-N 0.000 claims description 3
- 208000033116 Asbestos intoxication Diseases 0.000 claims description 3
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 3
- 206010014561 Emphysema Diseases 0.000 claims description 3
- 208000037487 Endotoxemia Diseases 0.000 claims description 3
- 201000009794 Idiopathic Pulmonary Fibrosis Diseases 0.000 claims description 3
- 206010063837 Reperfusion injury Diseases 0.000 claims description 3
- 206010040047 Sepsis Diseases 0.000 claims description 3
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 3
- 206010003441 asbestosis Diseases 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 208000036971 interstitial lung disease 2 Diseases 0.000 claims description 3
- 208000012947 ischemia reperfusion injury Diseases 0.000 claims description 3
- UWKABBHRKJCFIS-UHFFFAOYSA-N n-(2-hydroxy-3-phenoxypropoxy)benzamide Chemical compound C=1C=CC=CC=1OCC(O)CONC(=O)C1=CC=CC=C1 UWKABBHRKJCFIS-UHFFFAOYSA-N 0.000 claims description 3
- HPFQWCKXOZLYJQ-UHFFFAOYSA-N n-but-2-enoxy-3,4-difluoro-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC=CCONC(=O)C1=CC=C(F)C(F)=C1NC1=CC=C(I)C=C1C HPFQWCKXOZLYJQ-UHFFFAOYSA-N 0.000 claims description 3
- 208000023504 respiratory system disease Diseases 0.000 claims description 3
- 208000011580 syndromic disease Diseases 0.000 claims description 3
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 2
- GYSCBCSGKXNZRH-UHFFFAOYSA-N 1-benzothiophene-2-carboxamide Chemical compound C1=CC=C2SC(C(=O)N)=CC2=C1 GYSCBCSGKXNZRH-UHFFFAOYSA-N 0.000 claims description 2
- IWZZOJQMYWDXJN-UHFFFAOYSA-N 2,3,5-trifluoro-4-(4-iodo-2-methylanilino)benzoic acid Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C=C(C(O)=O)C(F)=C1F IWZZOJQMYWDXJN-UHFFFAOYSA-N 0.000 claims description 2
- GLQYKBQRDMOSAE-UHFFFAOYSA-N 2-(2,4-difluoroanilino)-3,4-difluoro-n-(1-hydroxypropan-2-yloxy)benzamide Chemical compound OCC(C)ONC(=O)C1=CC=C(F)C(F)=C1NC1=CC=C(F)C=C1F GLQYKBQRDMOSAE-UHFFFAOYSA-N 0.000 claims description 2
- QEIPHLNZHZGILN-UHFFFAOYSA-N 2-(2,4-difluoroanilino)-3,4-difluoro-n-(2-hydroxyethoxy)benzamide Chemical compound OCCONC(=O)C1=CC=C(F)C(F)=C1NC1=CC=C(F)C=C1F QEIPHLNZHZGILN-UHFFFAOYSA-N 0.000 claims description 2
- BZJWSLFAFFNFIW-UHFFFAOYSA-N 2-(2-bromo-4-iodoanilino)-3,4-difluoro-n-hydroxybenzamide Chemical compound ONC(=O)C1=CC=C(F)C(F)=C1NC1=CC=C(I)C=C1Br BZJWSLFAFFNFIW-UHFFFAOYSA-N 0.000 claims description 2
- AVIWCXSGNKPKKK-UHFFFAOYSA-N 2-(2-bromo-4-iodoanilino)-5-chloro-3,4-difluoro-n-hydroxybenzamide Chemical compound ONC(=O)C1=CC(Cl)=C(F)C(F)=C1NC1=CC=C(I)C=C1Br AVIWCXSGNKPKKK-UHFFFAOYSA-N 0.000 claims description 2
- NYKNXVUDYAFANQ-UHFFFAOYSA-N 2-(2-chloro-4-iodoanilino)-3,4,5-trifluoro-n-(2-hydroxy-2-methylpropoxy)benzamide Chemical compound CC(C)(O)CONC(=O)C1=CC(F)=C(F)C(F)=C1NC1=CC=C(I)C=C1Cl NYKNXVUDYAFANQ-UHFFFAOYSA-N 0.000 claims description 2
- ZZKOQGATWBZIBF-UHFFFAOYSA-N 2-(2-chloro-4-iodoanilino)-3,4,5-trifluoro-n-(2-hydroxybutoxy)benzamide Chemical compound CCC(O)CONC(=O)C1=CC(F)=C(F)C(F)=C1NC1=CC=C(I)C=C1Cl ZZKOQGATWBZIBF-UHFFFAOYSA-N 0.000 claims description 2
- HRQFWZFDBBAAEB-UHFFFAOYSA-N 2-(2-chloro-4-iodoanilino)-3,4,5-trifluoro-n-(2-methoxyethoxy)benzamide Chemical compound COCCONC(=O)C1=CC(F)=C(F)C(F)=C1NC1=CC=C(I)C=C1Cl HRQFWZFDBBAAEB-UHFFFAOYSA-N 0.000 claims description 2
- GUKVRAXQEMSHJI-UHFFFAOYSA-N 2-(2-chloro-4-iodoanilino)-3,4,5-trifluoro-n-(3-hydroxypropoxy)benzamide Chemical compound OCCCONC(=O)C1=CC(F)=C(F)C(F)=C1NC1=CC=C(I)C=C1Cl GUKVRAXQEMSHJI-UHFFFAOYSA-N 0.000 claims description 2
- UHGZLNZLHYXGIL-UHFFFAOYSA-N 2-(2-chloro-4-iodoanilino)-3,4,5-trifluoro-n-[2-(2-methoxyethoxy)ethoxy]benzamide Chemical compound COCCOCCONC(=O)C1=CC(F)=C(F)C(F)=C1NC1=CC=C(I)C=C1Cl UHGZLNZLHYXGIL-UHFFFAOYSA-N 0.000 claims description 2
- XARHQJOJXOWHIY-UHFFFAOYSA-N 2-(2-chloro-4-iodoanilino)-3,4-difluoro-n-(1-hydroxypropan-2-yloxy)benzamide Chemical compound OCC(C)ONC(=O)C1=CC=C(F)C(F)=C1NC1=CC=C(I)C=C1Cl XARHQJOJXOWHIY-UHFFFAOYSA-N 0.000 claims description 2
- BZJWWFVEWXJWDW-UHFFFAOYSA-N 2-(2-chloro-4-iodoanilino)-3,4-difluoro-n-(2-hydroxy-3-morpholin-4-ylpropoxy)benzamide Chemical compound C1COCCN1CC(O)CONC(=O)C1=CC=C(F)C(F)=C1NC1=CC=C(I)C=C1Cl BZJWWFVEWXJWDW-UHFFFAOYSA-N 0.000 claims description 2
- VVEBMFSULUFWDB-UHFFFAOYSA-N 2-(2-chloro-4-iodoanilino)-3,4-difluoro-n-(2-hydroxy-3-phenoxypropoxy)benzamide Chemical compound C=1C=CC=CC=1OCC(O)CONC(=O)C1=CC=C(F)C(F)=C1NC1=CC=C(I)C=C1Cl VVEBMFSULUFWDB-UHFFFAOYSA-N 0.000 claims description 2
- UFTBYBWYJKAHLK-UHFFFAOYSA-N 2-(2-chloro-4-iodoanilino)-3,4-difluoro-n-(2-hydroxybutoxy)benzamide Chemical compound CCC(O)CONC(=O)C1=CC=C(F)C(F)=C1NC1=CC=C(I)C=C1Cl UFTBYBWYJKAHLK-UHFFFAOYSA-N 0.000 claims description 2
- NXUSIIDZHWMSCV-UHFFFAOYSA-N 2-(2-chloro-4-iodoanilino)-3,4-difluoro-n-hydroxybenzamide Chemical compound ONC(=O)C1=CC=C(F)C(F)=C1NC1=CC=C(I)C=C1Cl NXUSIIDZHWMSCV-UHFFFAOYSA-N 0.000 claims description 2
- YVSLCRVTJGUKSV-UHFFFAOYSA-N 2-(2-chloro-4-iodoanilino)-n-(cyclopropylmethoxy)-3,4,5-trifluorobenzamide Chemical compound C=1C=C(I)C=C(Cl)C=1NC=1C(F)=C(F)C(F)=CC=1C(=O)NOCC1CC1 YVSLCRVTJGUKSV-UHFFFAOYSA-N 0.000 claims description 2
- DVENTWJICBBDAJ-UHFFFAOYSA-N 2-(2-chloro-4-iodoanilino)-n-(cyclopropylmethoxy)-4-fluorobenzamide Chemical compound C=1C=C(I)C=C(Cl)C=1NC1=CC(F)=CC=C1C(=O)NOCC1CC1 DVENTWJICBBDAJ-UHFFFAOYSA-N 0.000 claims description 2
- BOWUZVRUZUWLAM-UHFFFAOYSA-N 2-(2-chloro-4-iodoanilino)-n-ethoxy-4-nitrobenzamide Chemical compound CCONC(=O)C1=CC=C([N+]([O-])=O)C=C1NC1=CC=C(I)C=C1Cl BOWUZVRUZUWLAM-UHFFFAOYSA-N 0.000 claims description 2
- SHNRDYXLGNJCOC-UHFFFAOYSA-N 2-(2-chloro-4-iodoanilino)-n-hydroxy-4-methylbenzamide Chemical compound CC1=CC=C(C(=O)NO)C(NC=2C(=CC(I)=CC=2)Cl)=C1 SHNRDYXLGNJCOC-UHFFFAOYSA-N 0.000 claims description 2
- UOPHVVWHOCFXFI-UHFFFAOYSA-N 2-(2-fluoro-4-iodoanilino)-n-hydroxy-4-nitrobenzamide Chemical compound ONC(=O)C1=CC=C([N+]([O-])=O)C=C1NC1=CC=C(I)C=C1F UOPHVVWHOCFXFI-UHFFFAOYSA-N 0.000 claims description 2
- BYNKDEUDKDVPPJ-UHFFFAOYSA-N 2-(4-bromo-2-methylanilino)-3,4-difluoro-n-(2-methylprop-2-enoxy)benzamide Chemical compound CC(=C)CONC(=O)C1=CC=C(F)C(F)=C1NC1=CC=C(Br)C=C1C BYNKDEUDKDVPPJ-UHFFFAOYSA-N 0.000 claims description 2
- WGIDTTDBLPTUHP-UHFFFAOYSA-N 2-(4-bromo-2-methylanilino)-3,4-difluoro-n-methoxybenzamide Chemical compound CONC(=O)C1=CC=C(F)C(F)=C1NC1=CC=C(Br)C=C1C WGIDTTDBLPTUHP-UHFFFAOYSA-N 0.000 claims description 2
- LUDUVSBHPMEVQH-UHFFFAOYSA-N 2-(4-bromo-2-methylanilino)-3,4-difluoro-n-propan-2-yloxybenzamide Chemical compound CC(C)ONC(=O)C1=CC=C(F)C(F)=C1NC1=CC=C(Br)C=C1C LUDUVSBHPMEVQH-UHFFFAOYSA-N 0.000 claims description 2
- HNXJNPOQVWVOGW-UHFFFAOYSA-N 2-(4-bromo-2-methylanilino)-3,4-difluoro-n-propoxybenzamide Chemical compound CCCONC(=O)C1=CC=C(F)C(F)=C1NC1=CC=C(Br)C=C1C HNXJNPOQVWVOGW-UHFFFAOYSA-N 0.000 claims description 2
- QTCFRZPPKGEZKF-UHFFFAOYSA-N 2-(4-bromo-2-methylanilino)-n-(4,4-dimethylpent-2-ynoxy)-3,4-difluorobenzamide Chemical compound CC1=CC(Br)=CC=C1NC1=C(F)C(F)=CC=C1C(=O)NOCC#CC(C)(C)C QTCFRZPPKGEZKF-UHFFFAOYSA-N 0.000 claims description 2
- BHEYIPCYQCTTAR-UHFFFAOYSA-N 2-(4-bromo-2-methylanilino)-n-(cyclopropylmethoxy)-3,4-difluorobenzamide Chemical compound CC1=CC(Br)=CC=C1NC1=C(F)C(F)=CC=C1C(=O)NOCC1CC1 BHEYIPCYQCTTAR-UHFFFAOYSA-N 0.000 claims description 2
- LNTZEUIWPWPUGC-UHFFFAOYSA-N 2-(4-bromo-2-methylanilino)-n-but-3-yn-2-yloxy-3,4-difluorobenzamide Chemical compound C#CC(C)ONC(=O)C1=CC=C(F)C(F)=C1NC1=CC=C(Br)C=C1C LNTZEUIWPWPUGC-UHFFFAOYSA-N 0.000 claims description 2
- BZEJFQCJTPHNOF-UHFFFAOYSA-N 2-(4-bromo-2-methylanilino)-n-cyclopentyloxy-3,4-difluorobenzamide Chemical compound CC1=CC(Br)=CC=C1NC1=C(F)C(F)=CC=C1C(=O)NOC1CCCC1 BZEJFQCJTPHNOF-UHFFFAOYSA-N 0.000 claims description 2
- RIEBDTYRNZXSGY-UHFFFAOYSA-N 2-(4-chloro-2-fluoroanilino)-3,4-difluoro-n-(2-hydroxypropoxy)benzamide Chemical compound CC(O)CONC(=O)C1=CC=C(F)C(F)=C1NC1=CC=C(Cl)C=C1F RIEBDTYRNZXSGY-UHFFFAOYSA-N 0.000 claims description 2
- IKFIPTAQYKYMAC-UHFFFAOYSA-N 2-(4-chloro-2-fluoroanilino)-n-(2,3-dihydroxypropoxy)-3,4-difluorobenzamide Chemical compound OCC(O)CONC(=O)C1=CC=C(F)C(F)=C1NC1=CC=C(Cl)C=C1F IKFIPTAQYKYMAC-UHFFFAOYSA-N 0.000 claims description 2
- LFKXETJHTXTXSA-UHFFFAOYSA-N 2-(4-iodo-2-methylanilino)-5-nitrobenzoic acid Chemical compound CC1=CC(I)=CC=C1NC1=CC=C([N+]([O-])=O)C=C1C(O)=O LFKXETJHTXTXSA-UHFFFAOYSA-N 0.000 claims description 2
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Classifications
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/365—Lactones
- A61K31/366—Lactones having six-membered rings, e.g. delta-lactones
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
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- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
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- A61K31/365—Lactones
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- A—HUMAN NECESSITIES
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- 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
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- 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
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/12—Mucolytics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P9/08—Vasodilators for multiple indications
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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
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
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- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Immunology (AREA)
- Pulmonology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US28988101P | 2001-05-09 | 2001-05-09 | |
| US60289881 | 2001-05-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AU3821502A true AU3821502A (en) | 2002-11-14 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU38215/02A Abandoned AU3821502A (en) | 2001-05-09 | 2002-05-07 | Method of treating or inhibiting neutrophil chemotaxis by administering a mek inhibitor |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US6972298B2 (enEXAMPLES) |
| EP (1) | EP1262176A1 (enEXAMPLES) |
| JP (1) | JP2002332247A (enEXAMPLES) |
| KR (1) | KR20020085852A (enEXAMPLES) |
| CN (1) | CN1383823A (enEXAMPLES) |
| AU (1) | AU3821502A (enEXAMPLES) |
| CA (1) | CA2385412A1 (enEXAMPLES) |
| HU (1) | HUP0201542A3 (enEXAMPLES) |
| IL (1) | IL149462A0 (enEXAMPLES) |
| NZ (1) | NZ518726A (enEXAMPLES) |
| PL (1) | PL353785A1 (enEXAMPLES) |
| ZA (1) | ZA200203668B (enEXAMPLES) |
Families Citing this family (45)
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| US7632866B2 (en) * | 2002-10-21 | 2009-12-15 | Ramot At Tel Aviv University | Derivatives of N-phenylanthranilic acid and 2-benzimidazolone as potassium channel and/or neuron activity modulators |
| WO2005007616A1 (en) * | 2003-07-23 | 2005-01-27 | Warner-Lambert Company Llc | Diphenylamino ketone derivatives as mek inhibitors |
| US8084645B2 (en) | 2003-09-19 | 2011-12-27 | Chugai Seiyaku Kabushiki Kaisha | 4-phenylamino-benzaldoxime derivatives and uses thereof as mitogen-activated protein kinase kinase (MEK) inhibitors |
| CA2542210A1 (en) * | 2003-10-21 | 2005-05-06 | Warner-Lambert Company Llc | Polymorphic form of n-[(r)-2,3-dihydroxy-propoxy]-3,4-difluoro-2-(2-fluoro-4-iodophenylamino)-benzamide |
| CA2727841A1 (en) | 2004-06-11 | 2005-12-22 | Japan Tobacco Inc. | 5-amino-2,4,7-trioxo-3,4,7,8-tetrahydro-2h-pyrido [2, 3-d] pyrimidine derivatives and related compounds |
| US7378423B2 (en) | 2004-06-11 | 2008-05-27 | Japan Tobacco Inc. | Pyrimidine compound and medical use thereof |
| TWI361066B (en) | 2004-07-26 | 2012-04-01 | Chugai Pharmaceutical Co Ltd | 5-substituted-2-phenylamino benzamides as mek inhibitors |
| WO2006061712A2 (en) * | 2004-12-10 | 2006-06-15 | Pfizer Inc. | Use of mek inhibitors in treating abnormal cell growth |
| CN109053523B (zh) | 2005-10-07 | 2022-03-25 | 埃克塞利希斯股份有限公司 | 作为用于治疗增生性疾病的mek抑制剂的吖丁啶 |
| US8022217B2 (en) | 2006-07-31 | 2011-09-20 | Cadila Healthcare Limited | Compounds suitable as modulators of HDL |
| JP5311673B2 (ja) | 2006-12-14 | 2013-10-09 | エグゼリクシス， インコーポレイテッド | Ｍｅｋ阻害剤の使用方法 |
| EP2155659A1 (en) * | 2007-05-11 | 2010-02-24 | Bayer Schering Pharma Aktiengesellschaft | Substituted phenylamino-benzene derivatives useful for treating hyper-proliferative disorders and diseases associated with mitogen extracellular kinase activity |
| US8765815B2 (en) * | 2007-09-20 | 2014-07-01 | Ramot At Tel-Aviv University Ltd. | N-phenyl anthranilic acid derivatives and uses thereof |
| US8193182B2 (en) | 2008-01-04 | 2012-06-05 | Intellikine, Inc. | Substituted isoquinolin-1(2H)-ones, and methods of use thereof |
| KR101660050B1 (ko) | 2008-01-04 | 2016-09-26 | 인텔리카인, 엘엘씨 | 특정 화학 물질, 조성물 및 방법 |
| EP2475659B1 (en) | 2009-09-08 | 2015-10-28 | F.Hoffmann-La Roche Ag | 4-substituted pyridin-3-yl-carboxamide compounds and methods of use |
| PH12012501361A1 (en) | 2009-12-31 | 2012-10-22 | Centro Nac De Investigaciones Oncologicas Cnio | Tricyclic compounds for use as kinase inhibitors |
| ES2627703T3 (es) | 2010-01-22 | 2017-07-31 | Fundación Centro Nacional De Investigaciones Oncológicas Carlos Iii | Inhibidores de PI3·quinasa |
| EP2536720A1 (en) | 2010-02-18 | 2012-12-26 | Centro Nacional de Investigaciones Oncológicas (CNIO) | Triazolo [4, 5 - b]pyridin derivatives |
| WO2011121317A1 (en) | 2010-04-01 | 2011-10-06 | Centro Nacional De Investigaciones Oncologicas (Cnio) | Imidazo [2,1-b] [1,3,4] thiadiazoles as protein or lipid kinase inhibitors |
| CN103221043B (zh) | 2010-08-05 | 2016-04-06 | 卡斯西部储备大学 | 用于治疗神经元连接发育障碍的erk抑制剂 |
| US20120095060A1 (en) * | 2010-10-14 | 2012-04-19 | Hardie William D | Methods and compositions of mitogen-activated protein kinase (mapk) pathway inhibitors for treating pulmonary fibrosis |
| WO2012052745A1 (en) | 2010-10-21 | 2012-04-26 | Centro Nacional De Investigaciones Oncológicas (Cnio) | Combinations of pi3k inhibitors with a second anti -tumor agent |
| NZ612909A (en) | 2011-01-10 | 2015-09-25 | Infinity Pharmaceuticals Inc | Processes for preparing isoquinolinones and solid forms of isoquinolinones |
| WO2012098387A1 (en) | 2011-01-18 | 2012-07-26 | Centro Nacional De Investigaciones Oncológicas (Cnio) | 6, 7-ring-fused triazolo [4, 3 - b] pyridazine derivatives as pim inhibitors |
| MY179607A (en) | 2011-04-01 | 2020-11-11 | Genentech Inc | Combinations of akt inhibitor compounds and abiraterone, and methods of use |
| EP2524918A1 (en) | 2011-05-19 | 2012-11-21 | Centro Nacional de Investigaciones Oncológicas (CNIO) | Imidazopyrazines derivates as kinase inhibitors |
| CA2872979C (en) | 2011-05-19 | 2020-02-18 | Joaquin Pastor Fernandez | Macrocyclic compounds as protein kinase inhibitors |
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| PE20191818A1 (es) | 2012-10-12 | 2019-12-27 | Exelixis Inc | Proceso para la elaboracion de 1-({3,4-difluoro-2-[(2-fluoro-4-yodofenil)amino]fenil}carbonil)-3-[(2s)-piperidin-2-il]azetidin-3ol |
| PL2914296T5 (pl) | 2012-11-01 | 2022-01-17 | Infinity Pharmaceuticals, Inc. | Leczenie nowotworu z zastosowaniem modulatorów izoform kinazy PI3 |
| US20140120060A1 (en) * | 2012-11-01 | 2014-05-01 | Infinity Pharmaceuticals, Inc. | Treatment of rheumatoid arthritis and asthma using pi3 kinase inhibitors |
| CA2923835C (en) * | 2013-09-11 | 2022-11-29 | The Administrators Of The Tulane Educational Fund | Novel anthranilic amides and the use thereof |
| WO2015160975A2 (en) | 2014-04-16 | 2015-10-22 | Infinity Pharmaceuticals, Inc. | Combination therapies |
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| RU2757457C2 (ru) * | 2016-11-18 | 2021-10-18 | Систик Файбросис Фаундейшн | Пирролопиримидины в качестве потенциаторов мвтр |
| EP3694833A4 (en) * | 2017-10-09 | 2021-06-30 | Ramot at Tel-Aviv University Ltd. | TRPV1 AND POTASIC IONIC CHANNEL MODULATORS AND THEIR USES |
| WO2019204569A1 (en) * | 2018-04-20 | 2019-10-24 | Thomas Jefferson University | METHOD OF USING MeK INHIBITOR TO PREVENT RADIATION INDUCED FIBROSIS |
| TW202342018A (zh) | 2022-03-04 | 2023-11-01 | 美商奇奈特生物製藥公司 | Mek激酶抑制劑 |
| WO2025043043A2 (en) * | 2023-08-24 | 2025-02-27 | Musc Foundation For Research Development | Mek1 inhibitors and uses thereof |
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| US5525625A (en) * | 1995-01-24 | 1996-06-11 | Warner-Lambert Company | 2-(2-Amino-3-methoxyphenyl)-4-oxo-4H-[1]benzopyran for treating proliferative disorders |
| AU5610398A (en) * | 1997-02-28 | 1998-09-18 | Warner-Lambert Company | Method of treating or preventing septic shock by administering a mek inhibitor |
| JP2002511092A (ja) * | 1997-07-01 | 2002-04-09 | ワーナー−ランバート・コンパニー | ４−ブロモまたは４−ヨードフェニルアミノベンズヒドロキサム酸誘導体およびそのｍｅｋ阻害剤としての使用 |
| DE69836378T2 (de) * | 1997-07-01 | 2007-10-11 | Warner-Lambert Co. Llc | Benzoesäure- und Benzamid-Derivate von Anthranilsäure und ihre Anwendung als MEK-Inhibitoren |
| GB9726851D0 (en) * | 1997-12-19 | 1998-02-18 | Zeneca Ltd | Human signal transduction serine/threonine kinase |
| WO1999034792A1 (en) * | 1998-01-06 | 1999-07-15 | The General Hospital Corporation | Use of mek1 inhibitors as protective agents against damage due to ischemia |
| WO2000035435A1 (en) | 1998-12-15 | 2000-06-22 | Warner-Lambert Company | Use of a mek inhibitor for preventing transplant rejection |
| WO2000035436A2 (en) | 1998-12-16 | 2000-06-22 | Warner-Lambert Company | Treatment of arthritis with mek inhibitors |
| ID30250A (id) | 1998-12-22 | 2001-11-15 | Warner Lambert Co | Kemoterapi kombinasi |
| WO2000040235A2 (en) * | 1999-01-07 | 2000-07-13 | Warner-Lambert Company | Treatment of asthma with mek inhibitors |
| AU2203800A (en) | 1999-01-07 | 2000-07-24 | Warner-Lambert Company | Antiviral method using mek inhibitors |
| JP2002534498A (ja) * | 1999-01-13 | 2002-10-15 | ワーナー−ランバート・カンパニー | Ｍｅｋ阻害剤としてのベンゼンスルホンアミド誘導体およびその使用 |
| KR20020012315A (ko) | 1999-07-16 | 2002-02-15 | 로즈 암스트롱, 크리스틴 에이. 트러트웨인 | Ｍｅｋ 저해제를 사용한 만성 통증의 치료 방법 |
| DE10017480A1 (de) * | 2000-04-07 | 2001-10-11 | Transmit Technologietransfer | Verwendung von Substanzen, die als MEK Inhibitor wirken, zur Herstellung eines Arneimittels gegen DNA- und RNA-Viren |
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| YU2503A (sh) * | 2000-07-19 | 2006-05-25 | Warner-Lambert Company | Oksigenovani estri 4-jodo fenilamino benzhidroksamskih kiselina |
| US20040122058A1 (en) | 2001-03-06 | 2004-06-24 | Dorian Bevec | Use of specific compounds particularly kinase inhibitors for treating viral infections |
| CA2442015A1 (en) | 2001-03-22 | 2002-10-03 | Van Andel Institute | Anthrax lethal factor inhibits tumor growth and angiogenesis |
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- 2002-05-03 EP EP02009344A patent/EP1262176A1/en not_active Withdrawn
- 2002-05-06 CA CA002385412A patent/CA2385412A1/en not_active Abandoned
- 2002-05-07 AU AU38215/02A patent/AU3821502A/en not_active Abandoned
- 2002-05-08 HU HU0201542A patent/HUP0201542A3/hu unknown
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| PL353785A1 (en) | 2002-11-18 |
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| CA2385412A1 (en) | 2002-11-09 |
| JP2002332247A (ja) | 2002-11-22 |
| NZ518726A (en) | 2004-06-25 |
| CN1383823A (zh) | 2002-12-11 |
| HUP0201542A2 (hu) | 2003-01-28 |
| IL149462A0 (en) | 2002-11-10 |
| US20030055095A1 (en) | 2003-03-20 |
| EP1262176A1 (en) | 2002-12-04 |
| KR20020085852A (ko) | 2002-11-16 |
| HU0201542D0 (enEXAMPLES) | 2002-07-29 |
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