CA2338764A1 - Composes d'anilide substitues et methodes associees - Google Patents
Composes d'anilide substitues et methodes associees Download PDFInfo
- Publication number
- CA2338764A1 CA2338764A1 CA002338764A CA2338764A CA2338764A1 CA 2338764 A1 CA2338764 A1 CA 2338764A1 CA 002338764 A CA002338764 A CA 002338764A CA 2338764 A CA2338764 A CA 2338764A CA 2338764 A1 CA2338764 A1 CA 2338764A1
- Authority
- CA
- Canada
- Prior art keywords
- methoxyphenyl
- methylethyl
- ethoxy
- bis
- amino
- 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
- -1 anilide compounds Chemical class 0.000 title claims abstract description 47
- 238000000034 method Methods 0.000 title claims description 25
- 238000011282 treatment Methods 0.000 claims abstract description 16
- 230000001404 mediated effect Effects 0.000 claims abstract description 13
- 102100035875 C-C chemokine receptor type 5 Human genes 0.000 claims abstract 3
- 101710149870 C-C chemokine receptor type 5 Proteins 0.000 claims abstract 3
- 239000001257 hydrogen Substances 0.000 claims description 124
- 229910052739 hydrogen Inorganic materials 0.000 claims description 124
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 101
- 229910052760 oxygen Inorganic materials 0.000 claims description 84
- 239000001301 oxygen Substances 0.000 claims description 81
- 150000001875 compounds Chemical class 0.000 claims description 79
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 77
- 229910052757 nitrogen Inorganic materials 0.000 claims description 76
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 72
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 70
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 65
- 229910052717 sulfur Chemical group 0.000 claims description 60
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 53
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 48
- 239000011593 sulfur Chemical group 0.000 claims description 48
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 47
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 45
- 150000002431 hydrogen Chemical class 0.000 claims description 45
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 37
- 229910052736 halogen Inorganic materials 0.000 claims description 32
- 150000002367 halogens Chemical class 0.000 claims description 32
- 125000005842 heteroatom Chemical group 0.000 claims description 30
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 30
- 125000003118 aryl group Chemical group 0.000 claims description 28
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 26
- 229910020008 S(O) Inorganic materials 0.000 claims description 24
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 24
- 201000010099 disease Diseases 0.000 claims description 23
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 23
- 101001043818 Mus musculus Interleukin-31 receptor subunit alpha Proteins 0.000 claims description 18
- 125000003003 spiro group Chemical group 0.000 claims description 18
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 17
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 17
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 15
- 125000000623 heterocyclic group Chemical group 0.000 claims description 15
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 15
- 241000124008 Mammalia Species 0.000 claims description 14
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 14
- 125000001424 substituent group Chemical group 0.000 claims description 13
- 125000004434 sulfur atom Chemical group 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 201000001320 Atherosclerosis Diseases 0.000 claims description 10
- 208000006673 asthma Diseases 0.000 claims description 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 10
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 9
- 208000012657 Atopic disease Diseases 0.000 claims description 9
- 208000023275 Autoimmune disease Diseases 0.000 claims description 9
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 9
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 201000006417 multiple sclerosis Diseases 0.000 claims description 9
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 9
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 9
- 125000006569 (C5-C6) heterocyclic group Chemical group 0.000 claims description 8
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 8
- 201000004681 Psoriasis Diseases 0.000 claims description 8
- 230000003176 fibrotic effect Effects 0.000 claims description 8
- 201000000306 sarcoidosis Diseases 0.000 claims description 8
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 7
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 7
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 6
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims description 6
- 229920006395 saturated elastomer Polymers 0.000 claims description 6
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 6
- 150000001204 N-oxides Chemical class 0.000 claims description 5
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims description 5
- HPQRMLPZJAJDOJ-UHFFFAOYSA-N n-[4-methoxy-3-[2-(2,2,6,6-tetramethylpiperidin-1-yl)ethoxy]phenyl]-4-phenoxybenzamide Chemical compound C1=C(OCCN2C(CCCC2(C)C)(C)C)C(OC)=CC=C1NC(=O)C(C=C1)=CC=C1OC1=CC=CC=C1 HPQRMLPZJAJDOJ-UHFFFAOYSA-N 0.000 claims description 5
- 125000004043 oxo group Chemical group O=* 0.000 claims description 5
- DSDPFOXAJXKYPW-UHFFFAOYSA-N 4-benzoyl-n-[3-[3-[di(propan-2-yl)amino]propyl]-4-methoxyphenyl]benzamide Chemical compound C1=C(CCCN(C(C)C)C(C)C)C(OC)=CC=C1NC(=O)C1=CC=C(C(=O)C=2C=CC=CC=2)C=C1 DSDPFOXAJXKYPW-UHFFFAOYSA-N 0.000 claims description 4
- ANKMQZRVOPYYNG-UHFFFAOYSA-N 4-benzyl-n-[2-[2-(diethylamino)ethoxy]phenyl]benzamide Chemical compound CCN(CC)CCOC1=CC=CC=C1NC(=O)C(C=C1)=CC=C1CC1=CC=CC=C1 ANKMQZRVOPYYNG-UHFFFAOYSA-N 0.000 claims description 4
- RBVUFDKOWOOCBI-UHFFFAOYSA-N 4-benzyl-n-[3-[2-[di(propan-2-yl)amino]ethoxy]-4-methoxyphenyl]benzamide Chemical compound C1=C(OCCN(C(C)C)C(C)C)C(OC)=CC=C1NC(=O)C(C=C1)=CC=C1CC1=CC=CC=C1 RBVUFDKOWOOCBI-UHFFFAOYSA-N 0.000 claims description 4
- JCEHQMNMLWNXHW-UHFFFAOYSA-N 4-benzyl-n-[4-methoxy-3-[2-(2,2,6,6-tetramethylpiperidin-1-yl)ethoxy]phenyl]benzamide Chemical compound C1=C(OCCN2C(CCCC2(C)C)(C)C)C(OC)=CC=C1NC(=O)C(C=C1)=CC=C1CC1=CC=CC=C1 JCEHQMNMLWNXHW-UHFFFAOYSA-N 0.000 claims description 4
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 4
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 4
- 125000002950 monocyclic group Chemical group 0.000 claims description 4
- KDKPSJZMPVXYFN-UHFFFAOYSA-N n-[3-[2-(diethylamino)ethoxy]-4-methoxyphenyl]-3-phenoxybenzamide Chemical compound C1=C(OC)C(OCCN(CC)CC)=CC(NC(=O)C=2C=C(OC=3C=CC=CC=3)C=CC=2)=C1 KDKPSJZMPVXYFN-UHFFFAOYSA-N 0.000 claims description 4
- ZHFVCLXEVMOACX-UHFFFAOYSA-N n-[3-[2-(diethylamino)ethoxy]-4-methoxyphenyl]-4-phenoxybenzamide Chemical compound C1=C(OC)C(OCCN(CC)CC)=CC(NC(=O)C=2C=CC(OC=3C=CC=CC=3)=CC=2)=C1 ZHFVCLXEVMOACX-UHFFFAOYSA-N 0.000 claims description 4
- WGRPYHAUTNEMNB-UHFFFAOYSA-N n-[3-[2-[di(propan-2-yl)amino]ethoxy]-4-methoxyphenyl]-4-phenoxybenzamide Chemical compound C1=C(OCCN(C(C)C)C(C)C)C(OC)=CC=C1NC(=O)C(C=C1)=CC=C1OC1=CC=CC=C1 WGRPYHAUTNEMNB-UHFFFAOYSA-N 0.000 claims description 4
- BZALKVRGDXMCFN-UHFFFAOYSA-N n-[4-[2-(diethylamino)ethoxy]phenyl]-4-phenoxybenzamide Chemical compound C1=CC(OCCN(CC)CC)=CC=C1NC(=O)C(C=C1)=CC=C1OC1=CC=CC=C1 BZALKVRGDXMCFN-UHFFFAOYSA-N 0.000 claims description 4
- DDXHUANEGUTCOA-UHFFFAOYSA-N n-[4-methoxy-3-[2-(2,2,6,6-tetramethylpiperidin-1-yl)ethoxy]phenyl]-3-phenoxybenzamide Chemical compound C1=C(OCCN2C(CCCC2(C)C)(C)C)C(OC)=CC=C1NC(=O)C(C=1)=CC=CC=1OC1=CC=CC=C1 DDXHUANEGUTCOA-UHFFFAOYSA-N 0.000 claims description 4
- MYCAENNMJZGZCQ-UHFFFAOYSA-N n-[4-methoxy-3-[2-(2,2,6,6-tetramethylpiperidin-1-yl)ethoxy]phenyl]-4-(4-methylphenyl)sulfonyl-3-nitrobenzamide Chemical compound C1=C(OCCN2C(CCCC2(C)C)(C)C)C(OC)=CC=C1NC(=O)C(C=C1[N+]([O-])=O)=CC=C1S(=O)(=O)C1=CC=C(C)C=C1 MYCAENNMJZGZCQ-UHFFFAOYSA-N 0.000 claims description 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 3
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims description 3
- QWPFSBBOOLEEKX-UHFFFAOYSA-N 3-(butylamino)-n-[4-methoxy-3-[2-(2,2,6,6-tetramethylpiperidin-1-yl)ethoxy]phenyl]-4-phenoxy-5-sulfamoylbenzamide Chemical compound CCCCNC1=CC(C(=O)NC=2C=C(OCCN3C(CCCC3(C)C)(C)C)C(OC)=CC=2)=CC(S(N)(=O)=O)=C1OC1=CC=CC=C1 QWPFSBBOOLEEKX-UHFFFAOYSA-N 0.000 claims description 3
- NXLFPXRYFDBDDX-UHFFFAOYSA-N 3-benzoyl-n-[3-[2-[di(propan-2-yl)amino]ethoxy]-4-methoxyphenyl]benzamide Chemical compound C1=C(OCCN(C(C)C)C(C)C)C(OC)=CC=C1NC(=O)C1=CC=CC(C(=O)C=2C=CC=CC=2)=C1 NXLFPXRYFDBDDX-UHFFFAOYSA-N 0.000 claims description 3
- DUPAQVNUXWIONQ-UHFFFAOYSA-N 4-(4-chlorophenoxy)-n-[3-[2-[di(propan-2-yl)amino]ethoxy]-4-methoxyphenyl]-3-nitrobenzamide Chemical compound C1=C(OCCN(C(C)C)C(C)C)C(OC)=CC=C1NC(=O)C(C=C1[N+]([O-])=O)=CC=C1OC1=CC=C(Cl)C=C1 DUPAQVNUXWIONQ-UHFFFAOYSA-N 0.000 claims description 3
- XZILDIIBPYENMY-UHFFFAOYSA-N 4-(4-chlorophenoxy)-n-[4-methoxy-3-[2-(2,2,6,6-tetramethylpiperidin-1-yl)ethoxy]phenyl]-3-nitrobenzamide Chemical compound C1=C(OCCN2C(CCCC2(C)C)(C)C)C(OC)=CC=C1NC(=O)C(C=C1[N+]([O-])=O)=CC=C1OC1=CC=C(Cl)C=C1 XZILDIIBPYENMY-UHFFFAOYSA-N 0.000 claims description 3
- HJMZYRDKDMYJTC-UHFFFAOYSA-N 4-(benzenesulfinyl)-n-[3-[2-[di(propan-2-yl)amino]ethoxy]-4-methoxyphenyl]benzamide Chemical compound C1=C(OCCN(C(C)C)C(C)C)C(OC)=CC=C1NC(=O)C1=CC=C(S(=O)C=2C=CC=CC=2)C=C1 HJMZYRDKDMYJTC-UHFFFAOYSA-N 0.000 claims description 3
- PWOOEKJVFBONDK-UHFFFAOYSA-N 4-benzoyl-n-[4-methoxy-3-[2-(2,2,6,6-tetramethylpiperidin-1-yl)ethoxy]phenyl]benzamide Chemical compound C1=C(OCCN2C(CCCC2(C)C)(C)C)C(OC)=CC=C1NC(=O)C(C=C1)=CC=C1C(=O)C1=CC=CC=C1 PWOOEKJVFBONDK-UHFFFAOYSA-N 0.000 claims description 3
- JQXVNQZQHZMKQH-UHFFFAOYSA-N 4-benzyl-n-[4-[2-[di(propan-2-yl)amino]ethoxy]phenyl]benzamide Chemical compound C1=CC(OCCN(C(C)C)C(C)C)=CC=C1NC(=O)C(C=C1)=CC=C1CC1=CC=CC=C1 JQXVNQZQHZMKQH-UHFFFAOYSA-N 0.000 claims description 3
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 125000004423 acyloxy group Chemical group 0.000 claims description 3
- 125000002619 bicyclic group Chemical group 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- AMEUSIDKGVZCAQ-UHFFFAOYSA-N n-[1-[2-[di(propan-2-yl)amino]ethyl]-3,4-dihydro-2h-quinolin-7-yl]-4-phenoxybenzamide Chemical compound C1=C2N(CCN(C(C)C)C(C)C)CCCC2=CC=C1NC(=O)C(C=C1)=CC=C1OC1=CC=CC=C1 AMEUSIDKGVZCAQ-UHFFFAOYSA-N 0.000 claims description 3
- MIQFBUQABHRMOD-UHFFFAOYSA-N n-[3-[2-[di(propan-2-yl)amino]ethoxy]-4-methoxyphenyl]-4-[hydroxy(phenyl)methyl]benzamide Chemical compound C1=C(OCCN(C(C)C)C(C)C)C(OC)=CC=C1NC(=O)C1=CC=C(C(O)C=2C=CC=CC=2)C=C1 MIQFBUQABHRMOD-UHFFFAOYSA-N 0.000 claims description 3
- FTBZVFGKOBZEIF-UHFFFAOYSA-N n-[3-[2-[di(propan-2-yl)amino]ethoxy]phenyl]-4-phenoxybenzamide Chemical compound CC(C)N(C(C)C)CCOC1=CC=CC(NC(=O)C=2C=CC(OC=3C=CC=CC=3)=CC=2)=C1 FTBZVFGKOBZEIF-UHFFFAOYSA-N 0.000 claims description 3
- IUDMYGJFUIZCQF-UHFFFAOYSA-N n-[3-[3-[di(propan-2-yl)amino]propyl]-4-methoxyphenyl]-4-(4-methylphenyl)sulfonyl-3-nitrobenzamide Chemical compound C1=C(CCCN(C(C)C)C(C)C)C(OC)=CC=C1NC(=O)C1=CC=C(S(=O)(=O)C=2C=CC(C)=CC=2)C([N+]([O-])=O)=C1 IUDMYGJFUIZCQF-UHFFFAOYSA-N 0.000 claims description 3
- HUDPEMVLPBMFRV-UHFFFAOYSA-N n-[4-[2-[di(propan-2-yl)amino]ethoxy]phenyl]-3-phenoxybenzamide Chemical compound C1=CC(OCCN(C(C)C)C(C)C)=CC=C1NC(=O)C1=CC=CC(OC=2C=CC=CC=2)=C1 HUDPEMVLPBMFRV-UHFFFAOYSA-N 0.000 claims description 3
- ZHTBTDWAWKFIHJ-UHFFFAOYSA-N n-[4-methoxy-3-[2-(2,2,6,6-tetramethylpiperidin-1-yl)ethoxy]phenyl]-4-(quinoxalin-2-ylamino)benzamide Chemical compound COC1=CC=C(NC(=O)C=2C=CC(NC=3N=C4C=CC=CC4=NC=3)=CC=2)C=C1OCCN1C(C)(C)CCCC1(C)C ZHTBTDWAWKFIHJ-UHFFFAOYSA-N 0.000 claims description 3
- 229910052700 potassium Inorganic materials 0.000 claims description 3
- YMEOYFISKKNIJI-UHFFFAOYSA-N 4-(benzenesulfonyl)-n-[3-[2-[di(propan-2-yl)amino]ethoxy]-4-methoxyphenyl]benzamide Chemical compound C1=C(OCCN(C(C)C)C(C)C)C(OC)=CC=C1NC(=O)C1=CC=C(S(=O)(=O)C=2C=CC=CC=2)C=C1 YMEOYFISKKNIJI-UHFFFAOYSA-N 0.000 claims description 2
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- NBXWGRQWAPRTKJ-UHFFFAOYSA-N n-[3-[2-[di(propan-2-yl)amino]ethoxy]-4-methoxyphenyl]-3-phenoxybenzamide Chemical compound C1=C(OCCN(C(C)C)C(C)C)C(OC)=CC=C1NC(=O)C1=CC=CC(OC=2C=CC=CC=2)=C1 NBXWGRQWAPRTKJ-UHFFFAOYSA-N 0.000 claims description 2
- RTWFIJUHURFHCC-UHFFFAOYSA-N n-[3-[2-[di(propan-2-yl)amino]ethoxy]-4-methoxyphenyl]-4-(4-methylphenyl)sulfonyl-3-nitrobenzamide Chemical compound C1=C(OCCN(C(C)C)C(C)C)C(OC)=CC=C1NC(=O)C1=CC=C(S(=O)(=O)C=2C=CC(C)=CC=2)C([N+]([O-])=O)=C1 RTWFIJUHURFHCC-UHFFFAOYSA-N 0.000 claims description 2
- KMBHSNFIOUYDGG-UHFFFAOYSA-N n-[3-[2-[di(propan-2-yl)amino]ethoxy]-4-methoxyphenyl]-4-(n-methylanilino)benzamide Chemical compound C1=C(OCCN(C(C)C)C(C)C)C(OC)=CC=C1NC(=O)C1=CC=C(N(C)C=2C=CC=CC=2)C=C1 KMBHSNFIOUYDGG-UHFFFAOYSA-N 0.000 claims description 2
- LKXCPTCSHAEOFJ-UHFFFAOYSA-N n-[3-[2-[di(propan-2-yl)amino]ethoxy]-4-methoxyphenyl]-4-(quinoxalin-2-ylamino)benzamide Chemical compound C1=C(OCCN(C(C)C)C(C)C)C(OC)=CC=C1NC(=O)C(C=C1)=CC=C1NC1=CN=C(C=CC=C2)C2=N1 LKXCPTCSHAEOFJ-UHFFFAOYSA-N 0.000 claims description 2
- GFXVNMHJHWCSHI-UHFFFAOYSA-N n-[3-[2-[di(propan-2-yl)amino]ethoxy]-4-methoxyphenyl]-4-phenylsulfanylbenzamide Chemical compound C1=C(OCCN(C(C)C)C(C)C)C(OC)=CC=C1NC(=O)C(C=C1)=CC=C1SC1=CC=CC=C1 GFXVNMHJHWCSHI-UHFFFAOYSA-N 0.000 claims description 2
- DAQULUHOUBTENA-UHFFFAOYSA-N n-[3-[3-[di(propan-2-yl)amino]propyl]-4-methoxyphenyl]-3-phenoxybenzamide Chemical compound C1=C(CCCN(C(C)C)C(C)C)C(OC)=CC=C1NC(=O)C1=CC=CC(OC=2C=CC=CC=2)=C1 DAQULUHOUBTENA-UHFFFAOYSA-N 0.000 claims description 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 10
- LUZHOLXDLNVQIU-UHFFFAOYSA-N 2-benzyl-n-[3-[2-[di(propan-2-yl)amino]ethoxy]-4-methoxyphenyl]-1,3-thiazole-4-carboxamide;hydrochloride Chemical compound Cl.C1=C(OCCN(C(C)C)C(C)C)C(OC)=CC=C1NC(=O)C1=CSC(CC=2C=CC=CC=2)=N1 LUZHOLXDLNVQIU-UHFFFAOYSA-N 0.000 claims 2
- ZPORDFQYOROFTI-UHFFFAOYSA-N 3-(butylamino)-n-[3-[2-[di(propan-2-yl)amino]ethoxy]-4-methoxyphenyl]-4-phenoxy-5-sulfamoylbenzamide Chemical compound CCCCNC1=CC(C(=O)NC=2C=C(OCCN(C(C)C)C(C)C)C(OC)=CC=2)=CC(S(N)(=O)=O)=C1OC1=CC=CC=C1 ZPORDFQYOROFTI-UHFFFAOYSA-N 0.000 claims 2
- WHVPLTUCPRBJKW-UHFFFAOYSA-N 3-(butylamino)-n-[3-[3-[di(propan-2-yl)amino]propyl]-4-methoxyphenyl]-4-phenoxy-5-sulfamoylbenzamide Chemical compound CCCCNC1=CC(C(=O)NC=2C=C(CCCN(C(C)C)C(C)C)C(OC)=CC=2)=CC(S(N)(=O)=O)=C1OC1=CC=CC=C1 WHVPLTUCPRBJKW-UHFFFAOYSA-N 0.000 claims 2
- ZLSPLUVNJPVMNH-UHFFFAOYSA-N 4-(4-chlorophenoxy)-n-[3-[3-[di(propan-2-yl)amino]propyl]-4-methoxyphenyl]-3-nitrobenzamide Chemical compound C1=C(CCCN(C(C)C)C(C)C)C(OC)=CC=C1NC(=O)C(C=C1[N+]([O-])=O)=CC=C1OC1=CC=C(Cl)C=C1 ZLSPLUVNJPVMNH-UHFFFAOYSA-N 0.000 claims 2
- NHVCFUCBOFSBCS-UHFFFAOYSA-N 4-(4-chlorophenyl)sulfonyl-n-[3-[2-[di(propan-2-yl)amino]ethoxy]-4-methoxyphenyl]benzamide Chemical compound C1=C(OCCN(C(C)C)C(C)C)C(OC)=CC=C1NC(=O)C1=CC=C(S(=O)(=O)C=2C=CC(Cl)=CC=2)C=C1 NHVCFUCBOFSBCS-UHFFFAOYSA-N 0.000 claims 2
- PYWXPXPVXZUMKV-UHFFFAOYSA-N 4-anilino-n-[3-[2-[di(propan-2-yl)amino]ethoxy]-4-methoxyphenyl]benzamide Chemical compound C1=C(OCCN(C(C)C)C(C)C)C(OC)=CC=C1NC(=O)C(C=C1)=CC=C1NC1=CC=CC=C1 PYWXPXPVXZUMKV-UHFFFAOYSA-N 0.000 claims 2
- LXZQBQFSMOTHRO-UHFFFAOYSA-N 4-benzoyl-n-[3-[2-[di(propan-2-yl)amino]ethoxy]-4-methoxyphenyl]benzamide Chemical compound C1=C(OCCN(C(C)C)C(C)C)C(OC)=CC=C1NC(=O)C1=CC=C(C(=O)C=2C=CC=CC=2)C=C1 LXZQBQFSMOTHRO-UHFFFAOYSA-N 0.000 claims 2
- FZCQISAPNRPOHO-UHFFFAOYSA-N n-[3-[2-[di(propan-2-yl)amino]ethoxy]-4-methoxyphenyl]-4-(3-hydroxyphenoxy)benzamide Chemical compound C1=C(OCCN(C(C)C)C(C)C)C(OC)=CC=C1NC(=O)C(C=C1)=CC=C1OC1=CC=CC(O)=C1 FZCQISAPNRPOHO-UHFFFAOYSA-N 0.000 claims 2
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- C07C311/37—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
- C07C311/38—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring having sulfur atoms of sulfonamide groups and amino groups bound to carbon atoms of six-membered rings of the same carbon skeleton
- C07C311/39—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring having sulfur atoms of sulfonamide groups and amino groups bound to carbon atoms of six-membered rings of the same carbon skeleton having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/44—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/04—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms
- C07D215/06—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms having only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
- C07D241/50—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with hetero atoms directly attached to ring nitrogen atoms
- C07D241/54—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
- C07D265/34—1,4-Oxazines; Hydrogenated 1,4-oxazines condensed with carbocyclic rings
- C07D265/36—1,4-Oxazines; Hydrogenated 1,4-oxazines condensed with carbocyclic rings condensed with one six-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/10—Spiro-condensed systems
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Immunology (AREA)
- Pulmonology (AREA)
- Rheumatology (AREA)
- Dermatology (AREA)
- Pain & Pain Management (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Transplantation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Hydrogenated Pyridines (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Quinoline Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Pyridine Compounds (AREA)
Abstract
L'invention concerne des composés d'anilide substitués qui sont des modulateurs, des agonistes ou des antagonistes du récepteur CCR5. En outre, l'invention concerne le traitement et la prévention d'états pathologiques induits par CCR5.
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US9440698P | 1998-07-28 | 1998-07-28 | |
| US13415799P | 1999-05-14 | 1999-05-14 | |
| US60/134,157 | 1999-05-14 | ||
| US60/094,406 | 1999-05-14 | ||
| PCT/US1999/017121 WO2000006146A1 (fr) | 1998-07-28 | 1999-07-28 | Composes d'anilide substitues et methodes associees |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2338764A1 true CA2338764A1 (fr) | 2000-02-10 |
Family
ID=26788834
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002338764A Abandoned CA2338764A1 (fr) | 1998-07-28 | 1999-07-28 | Composes d'anilide substitues et methodes associees |
Country Status (13)
| Country | Link |
|---|---|
| EP (1) | EP1100485A4 (fr) |
| JP (1) | JP2002521436A (fr) |
| KR (1) | KR20010074779A (fr) |
| CN (1) | CN1310621A (fr) |
| AU (1) | AU5239299A (fr) |
| BR (1) | BR9912406A (fr) |
| CA (1) | CA2338764A1 (fr) |
| HU (1) | HUP0102752A3 (fr) |
| IL (1) | IL141028A0 (fr) |
| NO (1) | NO20010446L (fr) |
| PL (1) | PL345713A1 (fr) |
| TR (1) | TR200100267T2 (fr) |
| WO (1) | WO2000006146A1 (fr) |
Families Citing this family (40)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6025154A (en) | 1995-06-06 | 2000-02-15 | Human Genome Sciences, Inc. | Polynucleotides encoding human G-protein chemokine receptor HDGNR10 |
| BR0112856A (pt) * | 2000-07-31 | 2003-07-01 | Smithkline Beecham Plc | Método para o tratamento dos distúrbios, composto ou um sal ou solvato deste, processo para a preparação dos mesmos, composição farmacêutico, método de tratamento e/ou profilaxia de um ou mais dos distúrbios, uso de um composto, e, método para o tratamento de diabetes, grande depressão, depressão manìaca, ansiedade, esquizofrenia e distúrbios do sono, em mamìferos humanos e não humanos |
| WO2002034760A2 (fr) * | 2000-10-23 | 2002-05-02 | Smithkline Beecham Corporation | Composes et procedes |
| US7507767B2 (en) | 2001-02-08 | 2009-03-24 | Schering Corporation | Cannabinoid receptor ligands |
| US7067539B2 (en) | 2001-02-08 | 2006-06-27 | Schering Corporation | Cannabinoid receptor ligands |
| US7175988B2 (en) | 2001-02-09 | 2007-02-13 | Human Genome Sciences, Inc. | Human G-protein Chemokine Receptor (CCR5) HDGNR10 |
| CN100567266C (zh) | 2001-11-14 | 2009-12-09 | 先灵公司 | 类大麻苷受体配体 |
| US7393934B2 (en) | 2001-12-21 | 2008-07-01 | Human Genome Sciences, Inc. | Human G-protein chemokine receptor (CCR5) HDGNR10 |
| DE60319714T2 (de) | 2002-06-19 | 2009-04-02 | Schering Corp. | Agonisten des cannabinoidrezeptors |
| RU2366655C2 (ru) | 2003-03-14 | 2009-09-10 | Оно Фармасьютикал Ко., Лтд. | Азотсодержащие гетероциклические производные и лекарственные средства, содержащие их в качестве активного ингредиента |
| TW200505902A (en) | 2003-03-20 | 2005-02-16 | Schering Corp | Cannabinoid receptor ligands |
| WO2004092169A1 (fr) | 2003-04-18 | 2004-10-28 | Ono Pharmaceutical Co., Ltd. | Compose de spiropiperidine et son utilisation medicinale |
| JP4869072B2 (ja) * | 2003-11-14 | 2012-02-01 | バーテックス ファーマシューティカルズ インコーポレイテッド | Atp結合カセットトランスポーターのモジュレーターとして有用なチアゾールおよびオキサゾール |
| US7544803B2 (en) * | 2004-01-23 | 2009-06-09 | Amgen Inc. | Vanilloid receptor ligands and their use in treatments |
| EP1723178A4 (fr) | 2004-03-12 | 2007-12-12 | Human Genome Sciences Inc | Recepteur humain (ccr5) hdgnr10 de chimiokine de la proteine g |
| EP2374455A3 (fr) | 2004-08-19 | 2012-03-28 | Vertex Pharmaceuticals Incorporated | Modulateurs des recepteurs muscariniques |
| US7786141B2 (en) | 2004-08-19 | 2010-08-31 | Vertex Pharmaceuticals Incorporated | Dihydrospiroindene modulators of muscarinic receptors |
| US8143404B2 (en) | 2004-09-13 | 2012-03-27 | Ono Pharmaceutical Co., Ltd | Nitrogenous heterocylic derivative and medicine containing the same as an active ingredient |
| RU2007124373A (ru) | 2004-11-29 | 2009-01-10 | Вертекс Фармасьютикалз Инкорпорейтед (Us) | Модуляторы мускариновых рецептеров |
| EP1889622A4 (fr) | 2005-05-31 | 2009-12-23 | Ono Pharmaceutical Co | Compose de spiropiperidine et son utilisation medicinale |
| WO2007044565A2 (fr) * | 2005-10-06 | 2007-04-19 | University Of Massachusetts | Composition et synthese de nouveaux reactifs pour inhiber la replication du vih |
| EP2657235A1 (fr) | 2005-10-28 | 2013-10-30 | Ono Pharmaceutical Co., Ltd. | Composé contenant un groupe basique et son utilisation |
| WO2007058322A1 (fr) | 2005-11-18 | 2007-05-24 | Ono Pharmaceutical Co., Ltd. | Composé contenant un groupe basique et son utilisation |
| AU2006330866A1 (en) | 2005-12-22 | 2007-07-05 | Vertex Pharmaceuticals Incorporated | Modulators of muscarinic receptors |
| AU2007221214A1 (en) | 2006-02-22 | 2007-09-07 | Vertex Pharmaceuticals Incorporated | Modulators of muscarinic receptors |
| KR20080098070A (ko) | 2006-02-22 | 2008-11-06 | 버텍스 파마슈티칼스 인코포레이티드 | 무스카린성 수용체의 조절제로서의 스피로 축합된 피페리딘 |
| CA2644368A1 (fr) | 2006-03-10 | 2007-09-20 | Ono Pharmaceutical Co., Ltd. | Derive heterocyclique azote et agent pharmaceutique comprenant le derive en tant que principe actif |
| WO2007132846A1 (fr) | 2006-05-16 | 2007-11-22 | Ono Pharmaceutical Co., Ltd. | Composé ayant un groupe acide qui peut être protégé et utilisation dudit composé |
| CN101500565A (zh) | 2006-06-29 | 2009-08-05 | 弗特克斯药品有限公司 | 毒蕈碱性受体的调节剂 |
| JP5245827B2 (ja) | 2006-07-31 | 2013-07-24 | 小野薬品工業株式会社 | スピロ結合した環状基を含有する化合物およびその用途 |
| AU2007284548A1 (en) | 2006-08-15 | 2008-02-21 | Vertex Pharmaceuticals Incorporated | Modulators of muscarinic receptors |
| CA2660974A1 (fr) | 2006-08-18 | 2008-02-21 | Vertex Pharmaceuticals Incorporated | Modulateurs des recepteurs muscariniques |
| GB0625523D0 (en) | 2006-12-21 | 2007-01-31 | Ge Healthcare Ltd | In vivo imaging agents |
| JP2010540640A (ja) | 2007-10-03 | 2010-12-24 | バーテックス ファーマシューティカルズ インコーポレイテッド | ムスカリン作用性レセプターのモジュレーター |
| WO2010129351A1 (fr) | 2009-04-28 | 2010-11-11 | Schepens Eye Research Institute | Procédé pour identifier et pour traiter une dégénérescence maculaire liée à l'âge |
| WO2013024022A1 (fr) | 2011-08-12 | 2013-02-21 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Méthodes et compositions pharmaceutiques pour traiter l'hypertension pulmonaire |
| FR2984318B1 (fr) | 2011-12-16 | 2014-06-27 | Oreal | Coupleur de structure 7 amino-1,2,3,4-tetrahydroquinoleines cationiques, composition tinctoriale en comprenant, procedes et utilisations |
| FR2984323B1 (fr) | 2011-12-16 | 2019-08-30 | L'oreal | Coupleur de structure 7 amino-1,2,3,4-tetrahydroquinoleines, composition tinctoriale en comprenant, procedes et utilisations |
| FR3072286B1 (fr) | 2017-10-13 | 2022-08-12 | Oreal | 7-amino-1,2,3,4-tetrahydroquinoleines particuliers, procede et composition |
| US11629196B2 (en) | 2020-04-27 | 2023-04-18 | Incelldx, Inc. | Method of treating SARS-CoV-2-associated hypercytokinemia by administering a human monoclonal antibody (PRO-140) that inhibits CCR5/CCL5 binding interactions |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4173464A (en) * | 1976-05-07 | 1979-11-06 | Sumitomo Chemical Company, Limited | m-Phenoxybenzamide derivatives |
| ZA985542B (en) * | 1997-07-03 | 1999-04-07 | Smithkline Beecham Corp | Substituted benzanilides as CCR5 receptor ligands antiinflammatory agents and antiviral agents |
-
1999
- 1999-07-28 JP JP2000562001A patent/JP2002521436A/ja not_active Withdrawn
- 1999-07-28 CN CN99809041A patent/CN1310621A/zh active Pending
- 1999-07-28 AU AU52392/99A patent/AU5239299A/en not_active Abandoned
- 1999-07-28 EP EP99937589A patent/EP1100485A4/fr not_active Withdrawn
- 1999-07-28 BR BR9912406-8A patent/BR9912406A/pt not_active Application Discontinuation
- 1999-07-28 IL IL14102899A patent/IL141028A0/xx unknown
- 1999-07-28 WO PCT/US1999/017121 patent/WO2000006146A1/fr not_active Ceased
- 1999-07-28 KR KR1020017001173A patent/KR20010074779A/ko not_active Withdrawn
- 1999-07-28 PL PL99345713A patent/PL345713A1/xx not_active Application Discontinuation
- 1999-07-28 HU HU0102752A patent/HUP0102752A3/hu unknown
- 1999-07-28 TR TR2001/00267T patent/TR200100267T2/xx unknown
- 1999-07-28 CA CA002338764A patent/CA2338764A1/fr not_active Abandoned
-
2001
- 2001-01-26 NO NO20010446A patent/NO20010446L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| BR9912406A (pt) | 2001-04-24 |
| TR200100267T2 (tr) | 2001-09-21 |
| CN1310621A (zh) | 2001-08-29 |
| PL345713A1 (en) | 2002-01-02 |
| NO20010446D0 (no) | 2001-01-26 |
| KR20010074779A (ko) | 2001-08-09 |
| NO20010446L (no) | 2001-01-26 |
| WO2000006146A1 (fr) | 2000-02-10 |
| HUP0102752A2 (hu) | 2001-12-28 |
| IL141028A0 (en) | 2002-02-10 |
| AU5239299A (en) | 2000-02-21 |
| WO2000006146A9 (fr) | 2000-08-03 |
| JP2002521436A (ja) | 2002-07-16 |
| EP1100485A1 (fr) | 2001-05-23 |
| HUP0102752A3 (en) | 2002-11-28 |
| EP1100485A4 (fr) | 2004-06-09 |
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Legal Events
| Date | Code | Title | Description |
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| FZDE | Discontinued |