CA2358438A1 - Methode antivirale utilisant des inhibiteurs de mek - Google Patents
Methode antivirale utilisant des inhibiteurs de mek Download PDFInfo
- Publication number
- CA2358438A1 CA2358438A1 CA002358438A CA2358438A CA2358438A1 CA 2358438 A1 CA2358438 A1 CA 2358438A1 CA 002358438 A CA002358438 A CA 002358438A CA 2358438 A CA2358438 A CA 2358438A CA 2358438 A1 CA2358438 A1 CA 2358438A1
- Authority
- CA
- Canada
- Prior art keywords
- methyl
- phenylamino
- iodo
- benzamide
- difluoro
- 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 abstract description 55
- 239000002829 mitogen activated protein kinase inhibitor Substances 0.000 title claims abstract description 41
- 230000000840 anti-viral effect Effects 0.000 title claims description 17
- 208000036142 Viral infection Diseases 0.000 claims abstract description 24
- 230000009385 viral infection Effects 0.000 claims abstract description 24
- 229940124647 MEK inhibitor Drugs 0.000 claims abstract description 22
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims abstract description 15
- 238000011282 treatment Methods 0.000 claims abstract description 11
- -1 phenyl amine compound Chemical class 0.000 claims description 124
- 150000001875 compounds Chemical class 0.000 claims description 119
- 229910052739 hydrogen Inorganic materials 0.000 claims description 41
- 239000001257 hydrogen Substances 0.000 claims description 39
- 125000000217 alkyl group Chemical group 0.000 claims description 35
- 241000700605 Viruses Species 0.000 claims description 27
- 150000002431 hydrogen Chemical group 0.000 claims description 26
- 239000005711 Benzoic acid Substances 0.000 claims description 25
- 201000010099 disease Diseases 0.000 claims description 24
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 24
- 229910052760 oxygen Inorganic materials 0.000 claims description 22
- 241000124008 Mammalia Species 0.000 claims description 21
- 125000003118 aryl group Chemical group 0.000 claims description 21
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 21
- 125000005843 halogen group Chemical group 0.000 claims description 20
- 125000001072 heteroaryl group Chemical group 0.000 claims description 20
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 19
- 125000005842 heteroatom Chemical group 0.000 claims description 18
- 125000001153 fluoro group Chemical group F* 0.000 claims description 17
- 150000003839 salts Chemical class 0.000 claims description 16
- 229910052717 sulfur Inorganic materials 0.000 claims description 16
- 230000003612 virological effect Effects 0.000 claims description 16
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 15
- 150000001408 amides Chemical class 0.000 claims description 13
- 150000002148 esters Chemical class 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 125000004122 cyclic group Chemical group 0.000 claims description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
- 125000003342 alkenyl group Chemical group 0.000 claims description 11
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- 125000003282 alkyl amino group Chemical group 0.000 claims description 10
- 125000000304 alkynyl group Chemical group 0.000 claims description 10
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 125000000623 heterocyclic group Chemical group 0.000 claims description 9
- 229940002612 prodrug Drugs 0.000 claims description 9
- 239000000651 prodrug Substances 0.000 claims description 9
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 9
- VJNZMSLGVUSPCF-UHFFFAOYSA-N 5-bromo-2-(2-chloro-4-iodoanilino)-n-(cyclopropylmethoxy)-3,4-difluorobenzamide Chemical compound C1CC1CONC(=O)C=1C=C(Br)C(F)=C(F)C=1NC1=CC=C(I)C=C1Cl VJNZMSLGVUSPCF-UHFFFAOYSA-N 0.000 claims description 8
- UHAXDAKQGVISBZ-UHFFFAOYSA-N N-(cyclopropylmethoxy)-3,4,5-trifluoro-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=C(F)C=C1C(=O)NOCC1CC1 UHAXDAKQGVISBZ-UHFFFAOYSA-N 0.000 claims description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
- 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 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- BZSLAYDTMNXEOY-UHFFFAOYSA-N 2-(2-chloro-4-iodoanilino)-4-fluoro-n-hydroxybenzamide Chemical compound ONC(=O)C1=CC=C(F)C=C1NC1=CC=C(I)C=C1Cl BZSLAYDTMNXEOY-UHFFFAOYSA-N 0.000 claims description 5
- 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 5
- IIJDQEBBOFOXKL-UHFFFAOYSA-N 4-fluoro-2-(4-iodo-2-methylanilino)benzoic acid Chemical compound CC1=CC(I)=CC=C1NC1=CC(F)=CC=C1C(O)=O IIJDQEBBOFOXKL-UHFFFAOYSA-N 0.000 claims description 5
- HSDBAZASWXUUHX-UHFFFAOYSA-N 4-fluoro-n-hydroxy-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC(F)=CC=C1C(=O)NO HSDBAZASWXUUHX-UHFFFAOYSA-N 0.000 claims description 5
- BGKLFAQCHHCZRZ-UHFFFAOYSA-N 4-iodo-2-methylaniline Chemical compound CC1=CC(I)=CC=C1N BGKLFAQCHHCZRZ-UHFFFAOYSA-N 0.000 claims description 5
- IPJAGDMRFVGHCN-UHFFFAOYSA-N 5-bromo-3,4-difluoro-n-hydroxy-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=C(Br)C=C1C(=O)NO IPJAGDMRFVGHCN-UHFFFAOYSA-N 0.000 claims description 5
- JUVFXZWQSKISCB-UHFFFAOYSA-N 5-bromo-n-(cyclopropylmethoxy)-3,4-difluoro-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=C(Br)C=C1C(=O)NOCC1CC1 JUVFXZWQSKISCB-UHFFFAOYSA-N 0.000 claims description 5
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 5
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 4
- QFWCYNPOPKQOKV-UHFFFAOYSA-N 2-(2-amino-3-methoxyphenyl)chromen-4-one Chemical group COC1=CC=CC(C=2OC3=CC=CC=C3C(=O)C=2)=C1N QFWCYNPOPKQOKV-UHFFFAOYSA-N 0.000 claims description 4
- ROCRLSIAQQGIPN-UHFFFAOYSA-N 2-(2-chloro-4-iodoanilino)-n-(cyclobutylmethoxy)-3,4-difluorobenzamide Chemical compound C=1C=C(I)C=C(Cl)C=1NC1=C(F)C(F)=CC=C1C(=O)NOCC1CCC1 ROCRLSIAQQGIPN-UHFFFAOYSA-N 0.000 claims description 4
- SRMDAFUJVQJZFI-UHFFFAOYSA-N 5-bromo-2-(2-chloro-4-iodoanilino)-3,4-difluoro-n-hydroxybenzamide Chemical compound ONC(=O)C1=CC(Br)=C(F)C(F)=C1NC1=CC=C(I)C=C1Cl SRMDAFUJVQJZFI-UHFFFAOYSA-N 0.000 claims description 4
- NYSBUFZXTTZARS-UHFFFAOYSA-N 5-chloro-n-(cyclopropylmethoxy)-3,4-difluoro-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=C(Cl)C=C1C(=O)NOCC1CC1 NYSBUFZXTTZARS-UHFFFAOYSA-N 0.000 claims description 4
- 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 4
- 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 4
- 125000001246 bromo group Chemical group Br* 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
- DSFQOJWTJQNGSU-UHFFFAOYSA-N 5-bromo-2-(4-iodo-2-methylanilino)-n-[(4-sulfamoylphenyl)methyl]benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC=C(Br)C=C1C(=O)NCC1=CC=C(S(N)(=O)=O)C=C1 DSFQOJWTJQNGSU-UHFFFAOYSA-N 0.000 claims description 3
- WBQVEORRHAMIPY-UHFFFAOYSA-N 5-bromo-n-(cyclobutylmethoxy)-3,4-difluoro-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=C(Br)C=C1C(=O)NOCC1CCC1 WBQVEORRHAMIPY-UHFFFAOYSA-N 0.000 claims description 3
- YGRHTDDIYZYUDW-UHFFFAOYSA-N 5-chloro-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)=C(Cl)C=C1C(=O)NOCC1CC1 YGRHTDDIYZYUDW-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
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N benzyl alcohol Substances OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 claims description 3
- 125000006555 (C3-C5) cycloalkyl group Chemical group 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
- QBTVPUBNRWFMGL-UHFFFAOYSA-N 2-(4-bromo-2-methylanilino)-3,4-difluoro-n-(2-morpholin-4-ylethyl)benzamide Chemical compound CC1=CC(Br)=CC=C1NC1=C(F)C(F)=CC=C1C(=O)NCCN1CCOCC1 QBTVPUBNRWFMGL-UHFFFAOYSA-N 0.000 claims description 2
- DFYRJMXCUCOACA-UHFFFAOYSA-N 2-(4-bromo-2-methylanilino)-4-fluorobenzoic acid Chemical compound CC1=CC(Br)=CC=C1NC1=CC(F)=CC=C1C(O)=O DFYRJMXCUCOACA-UHFFFAOYSA-N 0.000 claims description 2
- RASWBMJSCOCCOP-UHFFFAOYSA-N 2-(4-bromo-2-methylanilino)-n-[3-(dimethylamino)propyl]-3,4-difluorobenzamide Chemical compound CN(C)CCCNC(=O)C1=CC=C(F)C(F)=C1NC1=CC=C(Br)C=C1C RASWBMJSCOCCOP-UHFFFAOYSA-N 0.000 claims description 2
- IPJKPORKWBURKZ-UHFFFAOYSA-N 2-(4-iodo-2-methylanilino)-4-nitrobenzoic acid Chemical compound CC1=CC(I)=CC=C1NC1=CC([N+]([O-])=O)=CC=C1C(O)=O IPJKPORKWBURKZ-UHFFFAOYSA-N 0.000 claims description 2
- OPSQYIMKGZTWMH-UHFFFAOYSA-N 2-(4-iodo-2-methylanilino)-5-methylbenzoic acid Chemical compound OC(=O)C1=CC(C)=CC=C1NC1=CC=C(I)C=C1C OPSQYIMKGZTWMH-UHFFFAOYSA-N 0.000 claims description 2
- FHXQAXYOKQYKHH-UHFFFAOYSA-N 2-(4-iodo-2-methylanilino)benzoic acid Chemical compound CC1=CC(I)=CC=C1NC1=CC=CC=C1C(O)=O FHXQAXYOKQYKHH-UHFFFAOYSA-N 0.000 claims description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- IKYHHUKKYADHCL-UHFFFAOYSA-N 3,4,5-trifluoro-2-(4-iodo-2-methylanilino)benzoic acid Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=C(F)C=C1C(O)=O IKYHHUKKYADHCL-UHFFFAOYSA-N 0.000 claims description 2
- FUDMVYZZNQDLOV-UHFFFAOYSA-N 3,4-difluoro-2-(4-iodo-2-methylanilino)-n-propoxybenzamide Chemical compound CCCONC(=O)C1=CC=C(F)C(F)=C1NC1=CC=C(I)C=C1C FUDMVYZZNQDLOV-UHFFFAOYSA-N 0.000 claims description 2
- XKKPRURDQYWGIU-UHFFFAOYSA-N 3,4-difluoro-n-(3-hydroxypropyl)-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=CC=C1C(=O)NCCCO XKKPRURDQYWGIU-UHFFFAOYSA-N 0.000 claims description 2
- ILYBIGUHBUIMMX-UHFFFAOYSA-N 3,4-difluoro-n-hydroxy-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=CC=C1C(=O)NO ILYBIGUHBUIMMX-UHFFFAOYSA-N 0.000 claims description 2
- KYPCIWQNEIGNMW-UHFFFAOYSA-N 4-fluoro-2-(4-iodo-2-methylanilino)-n-(2h-tetrazol-5-yl)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC(F)=CC=C1C(=O)NC1=NN=NN1 KYPCIWQNEIGNMW-UHFFFAOYSA-N 0.000 claims description 2
- RBSKNOAECVHCJC-UHFFFAOYSA-N 4-iodo-2-methyl-n-[2-(2h-tetrazol-5-yl)phenyl]aniline Chemical compound CC1=CC(I)=CC=C1NC1=CC=CC=C1C1=NN=NN1 RBSKNOAECVHCJC-UHFFFAOYSA-N 0.000 claims description 2
- ZMFXUELOZZCDTA-UHFFFAOYSA-N 5-bromo-2-(2-bromo-4-iodoanilino)-n-ethoxy-3,4-difluorobenzamide Chemical compound CCONC(=O)C1=CC(Br)=C(F)C(F)=C1NC1=CC=C(I)C=C1Br ZMFXUELOZZCDTA-UHFFFAOYSA-N 0.000 claims description 2
- HIDZKFBLBMEGIG-UHFFFAOYSA-N 5-bromo-2-(4-iodo-2-methylanilino)-n-(3-piperidin-1-ylpropyl)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC=C(Br)C=C1C(=O)NCCCN1CCCCC1 HIDZKFBLBMEGIG-UHFFFAOYSA-N 0.000 claims description 2
- BSFZRPNXKUHUAO-UHFFFAOYSA-N 5-bromo-2-(4-iodo-2-methylanilino)benzoic acid Chemical compound CC1=CC(I)=CC=C1NC1=CC=C(Br)C=C1C(O)=O BSFZRPNXKUHUAO-UHFFFAOYSA-N 0.000 claims description 2
- LOWHNAGNDJCFSR-UHFFFAOYSA-N 5-bromo-3,4-difluoro-2-(4-iodo-2-methylanilino)-n-(2-pyridin-4-ylethyl)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=C(Br)C=C1C(=O)NCCC1=CC=NC=C1 LOWHNAGNDJCFSR-UHFFFAOYSA-N 0.000 claims description 2
- RDSDFNHYHOTLTQ-UHFFFAOYSA-N 5-bromo-3,4-difluoro-2-(4-iodo-2-methylanilino)-n-(2-pyrrolidin-1-ylethyl)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=C(Br)C=C1C(=O)NCCN1CCCC1 RDSDFNHYHOTLTQ-UHFFFAOYSA-N 0.000 claims description 2
- CYHKFEHMDJDUCY-UHFFFAOYSA-N 5-bromo-3,4-difluoro-2-(4-iodo-2-methylanilino)-n-(pyridin-3-ylmethoxy)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=C(Br)C=C1C(=O)NOCC1=CC=CN=C1 CYHKFEHMDJDUCY-UHFFFAOYSA-N 0.000 claims description 2
- ZXCWXANNFFPFMA-UHFFFAOYSA-N 5-bromo-3,4-difluoro-2-(4-iodo-2-methylanilino)-n-[3-(3-methoxyphenyl)prop-2-ynoxy]benzamide Chemical compound COC1=CC=CC(C#CCONC(=O)C=2C(=C(F)C(F)=C(Br)C=2)NC=2C(=CC(I)=CC=2)C)=C1 ZXCWXANNFFPFMA-UHFFFAOYSA-N 0.000 claims description 2
- NCTFSDXSASAYPI-UHFFFAOYSA-N 5-bromo-3,4-difluoro-2-(4-iodo-2-methylanilino)-n-propan-2-yloxybenzamide Chemical compound CC(C)ONC(=O)C1=CC(Br)=C(F)C(F)=C1NC1=CC=C(I)C=C1C NCTFSDXSASAYPI-UHFFFAOYSA-N 0.000 claims description 2
- IHCADDZQYYEXFH-UHFFFAOYSA-N 5-bromo-3,4-difluoro-2-(4-iodo-2-methylanilino)benzoic acid Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=C(Br)C=C1C(O)=O IHCADDZQYYEXFH-UHFFFAOYSA-N 0.000 claims description 2
- CWFCDWVXNAFAHX-UHFFFAOYSA-N 5-bromo-3,4-difluoro-2-[(4-iodo-2-methylphenyl)methyl]-n-[5-(3-methoxyphenyl)-3-methylpent-2-en-4-ynoxy]benzamide Chemical compound COC1=CC=CC(C#CC(C)=CCONC(=O)C=2C(=C(F)C(F)=C(Br)C=2)CC=2C(=CC(I)=CC=2)C)=C1 CWFCDWVXNAFAHX-UHFFFAOYSA-N 0.000 claims description 2
- PHJXBTSQFDDWJS-UHFFFAOYSA-N 5-bromo-n-(cyclopropylmethoxy)-3,4-difluoro-2-(2-fluoro-4-iodoanilino)benzamide Chemical compound FC1=CC(I)=CC=C1NC1=C(F)C(F)=C(Br)C=C1C(=O)NOCC1CC1 PHJXBTSQFDDWJS-UHFFFAOYSA-N 0.000 claims description 2
- YUKGGEUVPFOCFI-UHFFFAOYSA-N 5-bromo-n-[3-(dimethylamino)propyl]-2-(4-iodo-2-methylanilino)benzamide Chemical compound CN(C)CCCNC(=O)C1=CC(Br)=CC=C1NC1=CC=C(I)C=C1C YUKGGEUVPFOCFI-UHFFFAOYSA-N 0.000 claims description 2
- MBXXUKAZBOOXOL-UHFFFAOYSA-N 5-chloro-2-(4-iodo-2-methylanilino)benzoic acid Chemical compound CC1=CC(I)=CC=C1NC1=CC=C(Cl)C=C1C(O)=O MBXXUKAZBOOXOL-UHFFFAOYSA-N 0.000 claims description 2
- FVMKNRIUORTHMN-UHFFFAOYSA-N 5-chloro-3,4-difluoro-2-(2-fluoro-4-iodoanilino)-n-hydroxybenzamide Chemical compound ONC(=O)C1=CC(Cl)=C(F)C(F)=C1NC1=CC=C(I)C=C1F FVMKNRIUORTHMN-UHFFFAOYSA-N 0.000 claims description 2
- STJGIOUQRPNOBU-UHFFFAOYSA-N 5-chloro-3,4-difluoro-2-(4-iodo-2-methylanilino)benzoic acid Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=C(Cl)C=C1C(O)=O STJGIOUQRPNOBU-UHFFFAOYSA-N 0.000 claims description 2
- LESLNRINHALPLQ-UHFFFAOYSA-N 5-chloro-3,4-difluoro-2-(4-iodoanilino)benzoic acid Chemical compound OC(=O)C1=CC(Cl)=C(F)C(F)=C1NC1=CC=C(I)C=C1 LESLNRINHALPLQ-UHFFFAOYSA-N 0.000 claims description 2
- HVYIBSVDNMZNKR-UHFFFAOYSA-N 5-chloro-n-(cyclopropylmethoxy)-3,4-difluoro-2-(4-iodoanilino)benzamide Chemical compound C=1C=C(I)C=CC=1NC1=C(F)C(F)=C(Cl)C=C1C(=O)NOCC1CC1 HVYIBSVDNMZNKR-UHFFFAOYSA-N 0.000 claims description 2
- LTGBDYINTUIVIR-UHFFFAOYSA-N 5-fluoro-2-(4-iodo-2-methylanilino)-n-(oxan-2-yloxy)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC=C(F)C=C1C(=O)NOC1OCCCC1 LTGBDYINTUIVIR-UHFFFAOYSA-N 0.000 claims description 2
- PPBHPHGQDGGSHX-UHFFFAOYSA-N 5-fluoro-2-(4-iodo-2-methylanilino)benzoic acid Chemical compound CC1=CC(I)=CC=C1NC1=CC=C(F)C=C1C(O)=O PPBHPHGQDGGSHX-UHFFFAOYSA-N 0.000 claims description 2
- KDWCTADZBWWBLF-UHFFFAOYSA-N 5-fluoro-n-[3-[4-(2-hydroxyethyl)piperazin-1-yl]propyl]-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC=C(F)C=C1C(=O)NCCCN1CCN(CCO)CC1 KDWCTADZBWWBLF-UHFFFAOYSA-N 0.000 claims description 2
- BHHBGJUZEPKYTF-UHFFFAOYSA-N CCCCONC(=O)C1=CC(Br)=C(F)C(F)=C1NC1=CC=C(I)C=C1C.CC=CCONC(=O)C1=CC(Br)=C(F)C(F)=C1NC1=CC=C(I)C=C1C Chemical compound CCCCONC(=O)C1=CC(Br)=C(F)C(F)=C1NC1=CC=C(I)C=C1C.CC=CCONC(=O)C1=CC(Br)=C(F)C(F)=C1NC1=CC=C(I)C=C1C BHHBGJUZEPKYTF-UHFFFAOYSA-N 0.000 claims description 2
- 150000001558 benzoic acid derivatives Chemical class 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 claims description 2
- 208000002672 hepatitis B Diseases 0.000 claims description 2
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- 229960003742 phenol Drugs 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 230000026731 phosphorylation Effects 0.000 description 1
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- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000013641 positive control Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
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- 125000006239 protecting group Chemical group 0.000 description 1
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- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
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- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
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- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 210000000664 rectum Anatomy 0.000 description 1
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- 229960000329 ribavirin Drugs 0.000 description 1
- HZCAHMRRMINHDJ-DBRKOABJSA-N ribavirin Natural products O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1N=CN=C1 HZCAHMRRMINHDJ-DBRKOABJSA-N 0.000 description 1
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- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
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- 239000002356 single layer Substances 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
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- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
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- 125000001424 substituent group Chemical group 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
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- 239000004094 surface-active agent Substances 0.000 description 1
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- 239000000454 talc Substances 0.000 description 1
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- 235000012222 talc Nutrition 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical group C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical compound CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
- KHVCOYGKHDJPBZ-WDCZJNDASA-N tetrahydrooxazine Chemical compound OC[C@H]1ONC[C@@H](O)[C@@H]1O KHVCOYGKHDJPBZ-WDCZJNDASA-N 0.000 description 1
- 125000003554 tetrahydropyrrolyl group Chemical group 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- 125000004299 tetrazol-5-yl group Chemical group [H]N1N=NC(*)=N1 0.000 description 1
- 150000003536 tetrazoles Chemical group 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000005301 thienylmethyl group Chemical group [H]C1=C([H])C([H])=C(S1)C([H])([H])* 0.000 description 1
- 125000005297 thienyloxy group Chemical group S1C(=CC=C1)O* 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 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
- 238000011200 topical administration Methods 0.000 description 1
- 229940100611 topical cream Drugs 0.000 description 1
- 238000002723 toxicity assay Methods 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 230000037317 transdermal delivery Effects 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 229940070710 valerate Drugs 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
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- 239000003981 vehicle Substances 0.000 description 1
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- 229960003636 vidarabine Drugs 0.000 description 1
- 210000002845 virion Anatomy 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1
Classifications
-
- 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
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/16—Antivirals for RNA viruses for influenza or rhinoviruses
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/20—Antivirals for DNA viruses
- A61P31/22—Antivirals for DNA viruses for herpes viruses
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Virology (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- Tropical Medicine & Parasitology (AREA)
- Pulmonology (AREA)
- AIDS & HIV (AREA)
- Biotechnology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyrane Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Pyridine Compounds (AREA)
Abstract
Cette invention se rapporte à une méthode de prévention ou de traitement d'infections virales consistant à administrer à un patient nécessitant un tel traitement une quantité efficace d'un inhibiteur des kinases MEK, et notamment une phénylamine représentée par les formules (I) et (II).
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11502699P | 1999-01-07 | 1999-01-07 | |
| US60/115,026 | 1999-01-07 | ||
| PCT/US1999/030484 WO2000040237A1 (fr) | 1999-01-07 | 1999-12-21 | Methode antivirale utilisant des inhibiteurs de mek |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2358438A1 true CA2358438A1 (fr) | 2000-07-13 |
Family
ID=22358895
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002358438A Abandoned CA2358438A1 (fr) | 1999-01-07 | 1999-12-21 | Methode antivirale utilisant des inhibiteurs de mek |
Country Status (8)
| Country | Link |
|---|---|
| EP (1) | EP1140067A1 (fr) |
| JP (1) | JP2002534381A (fr) |
| AU (1) | AU2203800A (fr) |
| CA (1) | CA2358438A1 (fr) |
| HU (1) | HUP0104933A3 (fr) |
| IL (1) | IL144103A0 (fr) |
| WO (1) | WO2000040237A1 (fr) |
| ZA (1) | ZA200104000B (fr) |
Families Citing this family (47)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HRP20010603A2 (en) * | 1999-02-24 | 2002-08-31 | Hoffmann La Roche | Phenyl-and pyridinyl derivatives |
| 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 |
| DZ3401A1 (fr) * | 2000-07-19 | 2002-01-24 | Warner Lambert Co | Esters oxygenes d'acides 4-iodophenylamino benzhydroxamiques |
| TWI259180B (en) * | 2000-08-08 | 2006-08-01 | Hoffmann La Roche | 4-Phenyl-pyridine derivatives |
| EP1201765A3 (fr) * | 2000-10-16 | 2003-08-27 | Axxima Pharmaceuticals Aktiengesellschaft | Kinases cellulaires impliqués dans l'infection par cytomégalovirus et leur inhibition |
| ATE345788T1 (de) * | 2001-03-06 | 2006-12-15 | Dorian Bevec | Verwendung von mek hemmern zur behandlung von virusvermitteltem hämorragischem schock oder fieber |
| IL149462A0 (en) | 2001-05-09 | 2002-11-10 | Warner Lambert Co | Method of treating or inhibiting neutrophil chemotaxis by administering a mek inhibitor |
| DE10138912A1 (de) * | 2001-08-08 | 2003-02-27 | Medinnova Ges Med Innovationen | Verwendung von Wirksubstanzen zur Prophylaxe und/oder Therapie von Viruserkrankungen sowie Testsystem zum Auffinden solcher Wirksubstanzen |
| US7235537B2 (en) | 2002-03-13 | 2007-06-26 | Array Biopharma, Inc. | N3 alkylated benzimidazole derivatives as MEK inhibitors |
| SG2013013339A (en) | 2002-03-13 | 2014-12-30 | Array Biopharma Inc | N3 alkylated benzimidazole derivatives as mek inhibitors |
| DOP2003000641A (es) | 2002-05-10 | 2003-11-15 | Pfizer | Inhibidores de las arn polimerasa dependiente de arn del virus de las hepatitis c y composiciones y tratamiento que los usan |
| US7538120B2 (en) | 2003-09-03 | 2009-05-26 | Array Biopharma Inc. | Method of treating inflammatory diseases |
| US7144907B2 (en) | 2003-09-03 | 2006-12-05 | Array Biopharma Inc. | Heterocyclic inhibitors of MEK and methods of use thereof |
| WO2005040098A1 (fr) | 2003-10-21 | 2005-05-06 | Warner-Lambert Company Llc | Forme polymorphe du n-[(r)-2,3-dihydroxy-propoxy]-3,4-difluoro-2-(2-fluoro-4-iodophenylamino)-benzamide |
| CA2546353A1 (fr) | 2003-11-19 | 2005-06-09 | Array Biopharma Inc. | Inhibiteurs bicycliques de mek, et leurs procedes d'utilisation |
| US7732616B2 (en) | 2003-11-19 | 2010-06-08 | Array Biopharma Inc. | Dihydropyridine and dihydropyridazine derivatives as inhibitors of MEK and methods of use thereof |
| US7517994B2 (en) | 2003-11-19 | 2009-04-14 | Array Biopharma Inc. | Heterocyclic inhibitors of MEK and methods of use thereof |
| CA2546754A1 (fr) | 2003-11-21 | 2005-06-09 | Array Biopharma Inc. | Inhibiteurs de la proteine kinase akt |
| AU2005252110B2 (en) | 2004-06-11 | 2008-09-04 | Shionogi & Co., Ltd. | 5-amino-2,4,7-trioxo-3,4,7,8-tetrahydro-2H-pyrido[2,3-D] pyrimidine derivatives and related compounds for the treatment of cancer |
| US7378423B2 (en) | 2004-06-11 | 2008-05-27 | Japan Tobacco Inc. | Pyrimidine compound and medical use thereof |
| SE0401969D0 (sv) * | 2004-08-02 | 2004-08-02 | Astrazeneca Ab | Piperidine derivatives |
| SG177981A1 (en) | 2005-05-18 | 2012-02-28 | Array Biopharma Inc | 4-(phenylamino)-6-oxo-1, 6-dihydropyridazine-3-carboxamide derivatives as mek inhibitors for the treatment of hyperproliferative diseases |
| HRP20110498T1 (hr) | 2005-10-07 | 2011-08-31 | Exelixis | Azetidini kao inhibitori mek za liječenje proliferativnih bolesti |
| US8063050B2 (en) | 2006-07-06 | 2011-11-22 | Array Biopharma Inc. | Hydroxylated and methoxylated pyrimidyl cyclopentanes as AKT protein kinase inhibitors |
| EP2049500B1 (fr) | 2006-07-06 | 2011-09-07 | Array Biopharma, Inc. | Cyclopenta [d] pyrimidines utiles en tant qu'inhibiteurs de la protéine kinase akt |
| US8329701B2 (en) | 2006-07-06 | 2012-12-11 | Array Biopharma Inc. | Dihydrofuro pyrimidines as AKT protein kinase inhibitors |
| ATE532789T1 (de) | 2006-07-06 | 2011-11-15 | Array Biopharma Inc | Dihydrothienopyrimidine als akt-proteinkinase- inhibitoren |
| WO2008076415A1 (fr) | 2006-12-14 | 2008-06-26 | Exelixis, Inc. | Procédés d'utilisation d'inhibiteurs de mek |
| CN101918373B (zh) | 2007-07-05 | 2013-06-05 | 阵列生物制药公司 | 作为akt蛋白激酶抑制剂的嘧啶基环戊烷 |
| US9409886B2 (en) | 2007-07-05 | 2016-08-09 | Array Biopharma Inc. | Pyrimidyl cyclopentanes as AKT protein kinase inhibitors |
| US8846683B2 (en) | 2007-07-05 | 2014-09-30 | Array Biopharma, Inc. | Pyrimidyl cyclopentanes as Akt protein kinase inhibitors |
| CN103396409B (zh) | 2007-07-05 | 2015-03-11 | 阵列生物制药公司 | 作为akt蛋白激酶抑制剂的嘧啶基环戊烷 |
| US8853216B2 (en) | 2008-01-09 | 2014-10-07 | Array Biopharma, Inc. | Hydroxylated pyrimidyl cyclopentane as AKT protein kinase inhibitor |
| NZ586346A (en) | 2008-01-09 | 2012-02-24 | Array Biopharma Inc | Hydroxylated pyrimidyl cyclopentanes as akt protein kinase inhibitors |
| US8993630B2 (en) | 2008-11-10 | 2015-03-31 | Bayer Intellectual Property Gmbh | Substituted sulphonamido phenoxybenzamides |
| US20120263714A1 (en) | 2009-10-21 | 2012-10-18 | Bayer Intellectual Property Gmbh | Substituted halophenoxybenzamide derivatives |
| EP2491015A1 (fr) | 2009-10-21 | 2012-08-29 | Bayer Pharma Aktiengesellschaft | Benzosulfonamides substitués |
| US20120269803A1 (en) | 2009-10-21 | 2012-10-25 | Bayer Intellectual Property Gmbh | Substituted benzosulphonamides |
| WO2011155898A1 (fr) * | 2010-06-11 | 2011-12-15 | Wadell Goeran | Nouveaux composés antiviraux |
| CN103282351A (zh) | 2010-10-29 | 2013-09-04 | 拜耳知识产权有限责任公司 | 取代的苯氧基吡啶 |
| KR102021157B1 (ko) | 2011-04-01 | 2019-09-11 | 제넨테크, 인크. | Akt 억제제 화합물 및 아비라테론의 조합물, 및 사용 방법 |
| TR201815685T4 (tr) | 2011-04-01 | 2018-11-21 | Genentech Inc | Kanser tedavisi için akt ve mek inhibe edici bileşiklerin kombinasyonları. |
| BR112015007616B1 (pt) * | 2012-10-08 | 2022-08-09 | Atriva Therapeutics Gmbh | Uso de inibidores de mek em combinação com oseltamivir, e composição farmacêutica e seu uso |
| MA38085B1 (fr) | 2012-10-12 | 2018-11-30 | Exelixis Inc | Nouveau procédé pour la production de composés à utiliser dans le traitement du cancer |
| CA2923835C (fr) | 2013-09-11 | 2022-11-29 | The Administrators Of The Tulane Educational Fund | Nouveaux amides anthraniliques et utilisation de ces derniers |
| US11903917B2 (en) * | 2017-10-17 | 2024-02-20 | Atriva Therapeutics Gmbh | MEK-inhibitor for the treatment of viral and bacterial infections |
| LU101183B1 (en) * | 2019-04-16 | 2020-10-16 | Atriva Therapeutics Gmbh | Novel mek-inhibitor for the treatment of viral and bacterial infections |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6420338B1 (en) * | 1997-06-13 | 2002-07-16 | New York University Medical Center | Inhibition of the Src kinase family pathway as a method of treating HBV infection and hepatocellular carcinoma |
| NZ501276A (en) * | 1997-07-01 | 2000-10-27 | Warner Lambert Co | 4-bromo or 4-iodo phenylamino benzhydroxamic acid derivatives and their use as MEK inhibitors in treating proliferative disorders |
| CA2290509A1 (fr) * | 1997-07-01 | 1999-01-14 | Warner-Lambert Company | Derives d'acide benzoique 2-(4-bromo ou 4-iodo phenylamino) et utilisation de ces derniers en tant qu'inhibiteurs de mek |
-
1999
- 1999-12-21 AU AU22038/00A patent/AU2203800A/en not_active Abandoned
- 1999-12-21 IL IL14410399A patent/IL144103A0/xx unknown
- 1999-12-21 CA CA002358438A patent/CA2358438A1/fr not_active Abandoned
- 1999-12-21 EP EP99966522A patent/EP1140067A1/fr not_active Withdrawn
- 1999-12-21 JP JP2000591994A patent/JP2002534381A/ja active Pending
- 1999-12-21 WO PCT/US1999/030484 patent/WO2000040237A1/fr not_active Ceased
- 1999-12-21 HU HU0104933A patent/HUP0104933A3/hu unknown
-
2001
- 2001-05-16 ZA ZA200104000A patent/ZA200104000B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ZA200104000B (en) | 2002-08-16 |
| AU2203800A (en) | 2000-07-24 |
| JP2002534381A (ja) | 2002-10-15 |
| HUP0104933A3 (en) | 2003-12-29 |
| IL144103A0 (en) | 2002-05-23 |
| WO2000040237A1 (fr) | 2000-07-13 |
| EP1140067A1 (fr) | 2001-10-10 |
| HUP0104933A2 (hu) | 2002-04-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |