JP2006502095A - Ｃ５ａ受容体モジュレーターとしての置換ビアリールアミド - Google Patents

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Publication number

JP2006502095A

JP2006502095A JP2003580294A JP2003580294A JP2006502095A JP 2006502095 A JP2006502095 A JP 2006502095A JP 2003580294 A JP2003580294 A JP 2003580294A JP 2003580294 A JP2003580294 A JP 2003580294A JP 2006502095 A JP2006502095 A JP 2006502095A

Authority

JP

Japan

Prior art keywords

alkyl

substituted

alkoxy

independently

hydroxy

Prior art date

2002-03-28

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.)

Withdrawn

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• -1 biaryl amides Chemical class 0.000 title claims abstract description 340
• 102000005590 Anaphylatoxin C5a Receptor Human genes 0.000 title claims abstract description 186
• 108010059426 Anaphylatoxin C5a Receptor Proteins 0.000 title claims abstract description 185
• 150000001875 compounds Chemical class 0.000 claims abstract description 330
• 230000000694 effects Effects 0.000 claims abstract description 75
• 238000000034 method Methods 0.000 claims abstract description 50
• 238000000338 in vitro Methods 0.000 claims abstract description 34
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 25
• 238000001727 in vivo Methods 0.000 claims abstract description 20
• 241001465754 Metazoa Species 0.000 claims abstract description 16
• 125000000217 alkyl group Chemical group 0.000 claims description 323
• 125000001424 substituent group Chemical group 0.000 claims description 264
• 229910052736 halogen Inorganic materials 0.000 claims description 250
• 150000002367 halogens Chemical class 0.000 claims description 246
• 125000001188 haloalkyl group Chemical group 0.000 claims description 214
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 186
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 175
• 150000003839 salts Chemical class 0.000 claims description 159
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 147
• 125000006413 ring segment Chemical group 0.000 claims description 112
• 125000003545 alkoxy group Chemical group 0.000 claims description 107
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 96
• 229910052760 oxygen Inorganic materials 0.000 claims description 83
• 102100031506 Complement C5 Human genes 0.000 claims description 81
• 238000003556 assay Methods 0.000 claims description 80
• 229910052717 sulfur Inorganic materials 0.000 claims description 80
• 101000941598 Homo sapiens Complement C5 Proteins 0.000 claims description 79
• 229910052799 carbon Inorganic materials 0.000 claims description 72
• 125000001544 thienyl group Chemical group 0.000 claims description 72
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 68
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 64
• 125000004414 alkyl thio group Chemical group 0.000 claims description 62
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 61
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 58
• 229920006395 saturated elastomer Polymers 0.000 claims description 55
• 230000027455 binding Effects 0.000 claims description 54
• 125000003118 aryl group Chemical group 0.000 claims description 53
• 239000000203 mixture Substances 0.000 claims description 51
• 210000004027 cell Anatomy 0.000 claims description 50
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 44
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 44
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 38
• 230000035605 chemotaxis Effects 0.000 claims description 37
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 36
• 239000000556 agonist Substances 0.000 claims description 35
• 125000001072 heteroaryl group Chemical group 0.000 claims description 35
• 230000001404 mediated effect Effects 0.000 claims description 33
• 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 28
• 229960005235 piperonyl butoxide Drugs 0.000 claims description 28
• 125000004591 piperonyl group Chemical group C(C1=CC=2OCOC2C=C1)* 0.000 claims description 28
• 229910052739 hydrogen Inorganic materials 0.000 claims description 27
• 239000001257 hydrogen Substances 0.000 claims description 27
• 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 26
• 230000027425 release of sequestered calcium ion into cytosol Effects 0.000 claims description 25
• 150000002431 hydrogen Chemical class 0.000 claims description 23
• 125000004076 pyridyl group Chemical group 0.000 claims description 23
• 229910052757 nitrogen Inorganic materials 0.000 claims description 21
• 125000003282 alkyl amino group Chemical group 0.000 claims description 19
• 125000004429 atom Chemical group 0.000 claims description 19
• 125000005842 heteroatom Chemical group 0.000 claims description 19
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 17
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 17
• 125000001624 naphthyl group Chemical group 0.000 claims description 17
• 125000004043 oxo group Chemical group O=* 0.000 claims description 17
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 17
• 125000004193 piperazinyl group Chemical group 0.000 claims description 16
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 15
• 125000000623 heterocyclic group Chemical group 0.000 claims description 15
• 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 15
• 125000002757 morpholinyl group Chemical group 0.000 claims description 15
• 125000003386 piperidinyl group Chemical group 0.000 claims description 15
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 15
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 15
• 125000001153 fluoro group Chemical group F* 0.000 claims description 13
• 239000000651 prodrug Substances 0.000 claims description 13
• 229940002612 prodrug Drugs 0.000 claims description 13
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 13
• 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 12
• 125000001041 indolyl group Chemical group 0.000 claims description 12
• 238000000159 protein binding assay Methods 0.000 claims description 12
• 230000019491 signal transduction Effects 0.000 claims description 12
• 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 11
• 125000006677 (C1-C3) haloalkoxy group Chemical group 0.000 claims description 10
• 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 10
• 210000000265 leukocyte Anatomy 0.000 claims description 10
• 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 10
• 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 9
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 9
• 125000002883 imidazolyl group Chemical group 0.000 claims description 9
• 230000002401 inhibitory effect Effects 0.000 claims description 9
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 9
• 125000000335 thiazolyl group Chemical group 0.000 claims description 9
• 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 8
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
• 239000001301 oxygen Substances 0.000 claims description 8
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 7
• 125000002971 oxazolyl group Chemical group 0.000 claims description 7
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 7
• 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims description 6
• 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 6
• 206010063837 Reperfusion injury Diseases 0.000 claims description 6
• 125000002541 furyl group Chemical group 0.000 claims description 6
• 125000005843 halogen group Chemical group 0.000 claims description 6
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 6
• 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims description 6
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
• 230000001413 cellular effect Effects 0.000 claims description 5
• 125000002861 (C1-C4) alkanoyl group Chemical group 0.000 claims description 4
• 201000001320 Atherosclerosis Diseases 0.000 claims description 4
• 208000024172 Cardiovascular disease Diseases 0.000 claims description 4
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
• 201000004681 Psoriasis Diseases 0.000 claims description 4
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
• 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 claims description 4
• 208000006673 asthma Diseases 0.000 claims description 4
• 125000006485 halo alkoxy phenyl group Chemical group 0.000 claims description 4
• 208000030603 inherited susceptibility to asthma Diseases 0.000 claims description 4
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 4
• 208000010125 myocardial infarction Diseases 0.000 claims description 4
• 206010039073 rheumatoid arthritis Diseases 0.000 claims description 4
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
• 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
• 208000006011 Stroke Diseases 0.000 claims description 3
• 125000005037 alkyl phenyl group Chemical group 0.000 claims description 3
• 208000012947 ischemia reperfusion injury Diseases 0.000 claims description 3
• 208000031225 myocardial ischemia Diseases 0.000 claims description 3
• VHMGLNZWVLWCLE-UHFFFAOYSA-N n-benzyl-n-(2,3-dihydro-1h-inden-2-yl)-2-methyl-6-phenylbenzamide Chemical compound C=1C=CC=CC=1CN(C1CC2=CC=CC=C2C1)C(=O)C=1C(C)=CC=CC=1C1=CC=CC=C1 VHMGLNZWVLWCLE-UHFFFAOYSA-N 0.000 claims description 3
• 125000003107 substituted aryl group Chemical group 0.000 claims description 3
• 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 3
• 239000011593 sulfur Substances 0.000 claims description 3
• 239000006188 syrup Substances 0.000 claims description 3
• 235000020357 syrup Nutrition 0.000 claims description 3
• 125000006728 (C1-C6) alkynyl group Chemical group 0.000 claims description 2
• 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
• 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 2
• YTMAESGDKJHTST-UHFFFAOYSA-N n-(1,3-benzodioxol-5-ylmethyl)-n-benzyl-2-[4-(trifluoromethyl)phenyl]benzamide Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=CC=CC=C1C(=O)N(CC=1C=C2OCOC2=CC=1)CC1=CC=CC=C1 YTMAESGDKJHTST-UHFFFAOYSA-N 0.000 claims description 2
• JMQSOEQIMIEPIL-UHFFFAOYSA-N n-(2,3-dihydro-1h-inden-2-yl)-n-[(2-fluorophenyl)methyl]-2-(5-methylthiophen-2-yl)naphthalene-1-carboxamide Chemical compound S1C(C)=CC=C1C1=CC=C(C=CC=C2)C2=C1C(=O)N(C1CC2=CC=CC=C2C1)CC1=CC=CC=C1F JMQSOEQIMIEPIL-UHFFFAOYSA-N 0.000 claims description 2
• DRJPUEBHZSFFFC-UHFFFAOYSA-N n-(2,3-dihydro-1h-inden-2-yl)-n-[(2-fluorophenyl)methyl]-2-hydroxynaphthalene-1-carboxamide Chemical compound OC1=CC=C2C=CC=CC2=C1C(=O)N(C1CC2=CC=CC=C2C1)CC1=CC=CC=C1F DRJPUEBHZSFFFC-UHFFFAOYSA-N 0.000 claims description 2
• GZFBFPOQDOLRSS-UHFFFAOYSA-N n-(2,3-dihydro-1h-inden-2-yl)-n-[(2-fluorophenyl)methyl]-2-methoxynaphthalene-1-carboxamide Chemical compound COC1=CC=C2C=CC=CC2=C1C(=O)N(C1CC2=CC=CC=C2C1)CC1=CC=CC=C1F GZFBFPOQDOLRSS-UHFFFAOYSA-N 0.000 claims description 2
• LFEHJNLHGXVHPA-UHFFFAOYSA-N n-benzyl-n-(2,3-dihydro-1h-inden-2-yl)-2-methoxynaphthalene-1-carboxamide Chemical compound COC1=CC=C2C=CC=CC2=C1C(=O)N(C1CC2=CC=CC=C2C1)CC1=CC=CC=C1 LFEHJNLHGXVHPA-UHFFFAOYSA-N 0.000 claims description 2
• WCKKBATUFCMDSP-UHFFFAOYSA-N n-benzyl-n-[(2-methylphenyl)methyl]-2-pyrrol-1-ylbenzamide Chemical compound CC1=CC=CC=C1CN(C(=O)C=1C(=CC=CC=1)N1C=CC=C1)CC1=CC=CC=C1 WCKKBATUFCMDSP-UHFFFAOYSA-N 0.000 claims description 2
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
• 239000006187 pill Substances 0.000 claims description 2
• 125000005936 piperidyl group Chemical group 0.000 claims description 2
• 125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims description 2
• 125000005301 thienylmethyl group Chemical group [H]C1=C([H])C([H])=C(S1)C([H])([H])* 0.000 claims description 2
• 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 claims 10
• 125000004130 indan-2-yl group Chemical group [H]C1=C([H])C([H])=C2C(=C1[H])C([H])([H])C([H])(*)C2([H])[H] 0.000 claims 10
• 125000002927 2-methoxybenzyl group Chemical group [H]C1=C([H])C([H])=C(C(OC([H])([H])[H])=C1[H])C([H])([H])* 0.000 claims 9
• 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims 8
• 125000006181 4-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])C([H])([H])* 0.000 claims 8
• 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims 7
• 125000006507 2,4-difluorobenzyl group Chemical group [H]C1=C(F)C([H])=C(F)C(=C1[H])C([H])([H])* 0.000 claims 5
• 125000006497 3-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C(OC([H])([H])[H])=C1[H])C([H])([H])* 0.000 claims 4
• 125000000579 2,2-diphenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(C1=C([H])C([H])=C([H])C([H])=C1[H])C([H])([H])* 0.000 claims 3
• 125000006179 2-methyl benzyl group Chemical group [H]C1=C([H])C(=C(C([H])=C1[H])C([H])([H])*)C([H])([H])[H] 0.000 claims 3
• 125000006186 3,5-dimethyl benzyl group Chemical group [H]C1=C(C([H])=C(C([H])=C1C([H])([H])[H])C([H])([H])*)C([H])([H])[H] 0.000 claims 2
• KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 2
• KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 2
• 125000006498 halo alkoxy benzyl group Chemical group 0.000 claims 2
• XIMAHGDXRNAODX-UHFFFAOYSA-N n-(2,3-dihydro-1h-inden-2-yl)-2-methoxy-n-[(3-methoxyphenyl)methyl]naphthalene-1-carboxamide Chemical compound COC1=CC=CC(CN(C2CC3=CC=CC=C3C2)C(=O)C=2C3=CC=CC=C3C=CC=2OC)=C1 XIMAHGDXRNAODX-UHFFFAOYSA-N 0.000 claims 2
• XTFIVUDBNACUBN-UHFFFAOYSA-N 1,3,5-trinitro-1,3,5-triazinane Chemical group [O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)C1 XTFIVUDBNACUBN-UHFFFAOYSA-N 0.000 claims 1
• YPODEHLMDRNVCM-UHFFFAOYSA-N 2-(3-acetamidophenyl)-n,n-dibenzylbenzamide Chemical compound CC(=O)NC1=CC=CC(C=2C(=CC=CC=2)C(=O)N(CC=2C=CC=CC=2)CC=2C=CC=CC=2)=C1 YPODEHLMDRNVCM-UHFFFAOYSA-N 0.000 claims 1
• 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims 1
• 125000003890 2-phenylbutyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 claims 1
• 125000006180 3-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1[H])C([H])([H])[H])C([H])([H])* 0.000 claims 1
• JEDICTNUQVTWDG-UHFFFAOYSA-N 4-[[2,3-dihydro-1h-inden-2-yl-(2-methoxynaphthalene-1-carbonyl)amino]methyl]benzoic acid Chemical compound COC1=CC=C2C=CC=CC2=C1C(=O)N(C1CC2=CC=CC=C2C1)CC1=CC=C(C(O)=O)C=C1 JEDICTNUQVTWDG-UHFFFAOYSA-N 0.000 claims 1
• 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims 1
• PRPUVGVCKNGUNT-UHFFFAOYSA-N 5-chloro-n-(2,3-dihydro-1h-inden-2-yl)-2-phenyl-n-(2-phenylethyl)benzamide Chemical compound C=1C=CC=CC=1CCN(C1CC2=CC=CC=C2C1)C(=O)C1=CC(Cl)=CC=C1C1=CC=CC=C1 PRPUVGVCKNGUNT-UHFFFAOYSA-N 0.000 claims 1
• PSRLIZKHLVPQHZ-UHFFFAOYSA-N 5-chloro-n-(2,3-dihydro-1h-inden-2-yl)-n-[(2-fluorophenyl)methyl]-2-phenylbenzamide Chemical compound FC1=CC=CC=C1CN(C(=O)C=1C(=CC=C(Cl)C=1)C=1C=CC=CC=1)C1CC2=CC=CC=C2C1 PSRLIZKHLVPQHZ-UHFFFAOYSA-N 0.000 claims 1
• ZWBGCLAPSOZQMP-UHFFFAOYSA-N 5-chloro-n-(2,3-dihydro-1h-inden-2-yl)-n-[(3-fluorophenyl)methyl]-2-phenylbenzamide Chemical compound FC1=CC=CC(CN(C2CC3=CC=CC=C3C2)C(=O)C=2C(=CC=C(Cl)C=2)C=2C=CC=CC=2)=C1 ZWBGCLAPSOZQMP-UHFFFAOYSA-N 0.000 claims 1
• ZWYVWARMRBYNKM-UHFFFAOYSA-N 5-chloro-n-(2,3-dihydro-1h-inden-2-yl)-n-[(3-methoxyphenyl)methyl]-2-phenylbenzamide Chemical compound COC1=CC=CC(CN(C2CC3=CC=CC=C3C2)C(=O)C=2C(=CC=C(Cl)C=2)C=2C=CC=CC=2)=C1 ZWYVWARMRBYNKM-UHFFFAOYSA-N 0.000 claims 1
• AIYHJGBNBBYDKW-UHFFFAOYSA-N 5-chloro-n-(2,3-dihydro-1h-inden-2-yl)-n-[(3-methylphenyl)methyl]-2-phenylbenzamide Chemical compound CC1=CC=CC(CN(C2CC3=CC=CC=C3C2)C(=O)C=2C(=CC=C(Cl)C=2)C=2C=CC=CC=2)=C1 AIYHJGBNBBYDKW-UHFFFAOYSA-N 0.000 claims 1
• OYACMTSRYCBMCY-UHFFFAOYSA-N 5-chloro-n-(2,3-dihydro-1h-inden-2-yl)-n-[(4-fluorophenyl)methyl]-2-phenylbenzamide Chemical compound C1=CC(F)=CC=C1CN(C(=O)C=1C(=CC=C(Cl)C=1)C=1C=CC=CC=1)C1CC2=CC=CC=C2C1 OYACMTSRYCBMCY-UHFFFAOYSA-N 0.000 claims 1
• BJEKFYWKWNZXTK-UHFFFAOYSA-N 5-chloro-n-(2,3-dihydro-1h-inden-2-yl)-n-[(4-methoxyphenyl)methyl]-2-phenylbenzamide Chemical compound C1=CC(OC)=CC=C1CN(C(=O)C=1C(=CC=C(Cl)C=1)C=1C=CC=CC=1)C1CC2=CC=CC=C2C1 BJEKFYWKWNZXTK-UHFFFAOYSA-N 0.000 claims 1
• KLUBHMKMCLVFPC-UHFFFAOYSA-N 5-chloro-n-(2,3-dihydro-1h-inden-2-yl)-n-[(4-methylphenyl)methyl]-2-phenylbenzamide Chemical compound C1=CC(C)=CC=C1CN(C(=O)C=1C(=CC=C(Cl)C=1)C=1C=CC=CC=1)C1CC2=CC=CC=C2C1 KLUBHMKMCLVFPC-UHFFFAOYSA-N 0.000 claims 1
• CLSWQRFHZWIHCZ-UHFFFAOYSA-N 5-chloro-n-[(3,4-difluorophenyl)methyl]-n-(2,3-dihydro-1h-inden-2-yl)-2-phenylbenzamide Chemical compound C1=C(F)C(F)=CC=C1CN(C(=O)C=1C(=CC=C(Cl)C=1)C=1C=CC=CC=1)C1CC2=CC=CC=C2C1 CLSWQRFHZWIHCZ-UHFFFAOYSA-N 0.000 claims 1
• HHJACKUDLFYPHJ-UHFFFAOYSA-N 5-chloro-n-[(3-methoxyphenyl)methyl]-2-phenyl-n-(2-phenylethyl)benzamide Chemical compound COC1=CC=CC(CN(CCC=2C=CC=CC=2)C(=O)C=2C(=CC=C(Cl)C=2)C=2C=CC=CC=2)=C1 HHJACKUDLFYPHJ-UHFFFAOYSA-N 0.000 claims 1
• 239000000443 aerosol Substances 0.000 claims 1
• 125000005907 alkyl ester group Chemical group 0.000 claims 1
• 239000002775 capsule Substances 0.000 claims 1
• 239000006071 cream Substances 0.000 claims 1
• 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims 1
• 239000012530 fluid Substances 0.000 claims 1
• 239000000499 gel Substances 0.000 claims 1
• 125000004129 indan-1-yl group Chemical group [H]C1=C([H])C([H])=C2C(=C1[H])C([H])([H])C([H])([H])C2([H])* 0.000 claims 1
• PQIOSYKVBBWRRI-UHFFFAOYSA-N methylphosphonyl difluoride Chemical group CP(F)(F)=O PQIOSYKVBBWRRI-UHFFFAOYSA-N 0.000 claims 1
• NIFRRAYVYJKLCV-UHFFFAOYSA-N n,n-dibenzyl-2-(2,3-dichlorophenyl)benzamide Chemical compound ClC1=CC=CC(C=2C(=CC=CC=2)C(=O)N(CC=2C=CC=CC=2)CC=2C=CC=CC=2)=C1Cl NIFRRAYVYJKLCV-UHFFFAOYSA-N 0.000 claims 1
• PTSIAUYIVYYSHO-UHFFFAOYSA-N n,n-dibenzyl-2-(2,4-dichlorophenyl)benzamide Chemical compound ClC1=CC(Cl)=CC=C1C1=CC=CC=C1C(=O)N(CC=1C=CC=CC=1)CC1=CC=CC=C1 PTSIAUYIVYYSHO-UHFFFAOYSA-N 0.000 claims 1
• STDRIBGDZUDOMU-UHFFFAOYSA-N n,n-dibenzyl-2-(2,4-dimethoxyphenyl)benzamide Chemical compound COC1=CC(OC)=CC=C1C1=CC=CC=C1C(=O)N(CC=1C=CC=CC=1)CC1=CC=CC=C1 STDRIBGDZUDOMU-UHFFFAOYSA-N 0.000 claims 1
• QVYZZQHABCSKIE-UHFFFAOYSA-N n,n-dibenzyl-2-(2-chlorophenyl)benzamide Chemical compound ClC1=CC=CC=C1C1=CC=CC=C1C(=O)N(CC=1C=CC=CC=1)CC1=CC=CC=C1 QVYZZQHABCSKIE-UHFFFAOYSA-N 0.000 claims 1
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• ZFKYAFZDACUXRY-UHFFFAOYSA-N n,n-dibenzyl-2-phenylbenzamide Chemical compound C=1C=CC=C(C=2C=CC=CC=2)C=1C(=O)N(CC=1C=CC=CC=1)CC1=CC=CC=C1 ZFKYAFZDACUXRY-UHFFFAOYSA-N 0.000 claims 1
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• ITMFYQLNJVXSDP-UHFFFAOYSA-N n-(1,3-benzodioxol-5-ylmethyl)-n-(2,3-dihydro-1h-inden-2-yl)-2-(3-methoxyphenyl)benzamide Chemical compound COC1=CC=CC(C=2C(=CC=CC=2)C(=O)N(CC=2C=C3OCOC3=CC=2)C2CC3=CC=CC=C3C2)=C1 ITMFYQLNJVXSDP-UHFFFAOYSA-N 0.000 claims 1
• LPFYXJDHQXABLI-UHFFFAOYSA-N n-(1,3-benzodioxol-5-ylmethyl)-n-(2,3-dihydro-1h-inden-2-yl)-2-methoxynaphthalene-1-carboxamide Chemical compound C1C2=CC=CC=C2CC1N(CC=1C=C2OCOC2=CC=1)C(=O)C1=C2C=CC=CC2=CC=C1OC LPFYXJDHQXABLI-UHFFFAOYSA-N 0.000 claims 1
• SQLVYAFGGJAIHC-UHFFFAOYSA-N n-(1,3-benzodioxol-5-ylmethyl)-n-(2,3-dihydro-1h-inden-2-yl)-2-methyl-6-phenylbenzamide Chemical compound C=1C=C2OCOC2=CC=1CN(C1CC2=CC=CC=C2C1)C(=O)C=1C(C)=CC=CC=1C1=CC=CC=C1 SQLVYAFGGJAIHC-UHFFFAOYSA-N 0.000 claims 1
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• XMDYUNIDUPSQRS-UHFFFAOYSA-N n-(1,3-benzodioxol-5-ylmethyl)-n-(2,3-dihydro-1h-inden-2-yl)-9h-fluorene-4-carboxamide Chemical compound C1C2=CC=CC=C2C2=C1C=CC=C2C(=O)N(C1CC2=CC=CC=C2C1)CC1=CC=C(OCO2)C2=C1 XMDYUNIDUPSQRS-UHFFFAOYSA-N 0.000 claims 1
• ITBHUMRLUIVISY-UHFFFAOYSA-N n-(2,3-dihydro-1h-inden-2-yl)-2-(2-fluorophenyl)-n-[(2-methoxyphenyl)methyl]benzamide Chemical compound COC1=CC=CC=C1CN(C(=O)C=1C(=CC=CC=1)C=1C(=CC=CC=1)F)C1CC2=CC=CC=C2C1 ITBHUMRLUIVISY-UHFFFAOYSA-N 0.000 claims 1
• VTCZXXXQDSOQFR-UHFFFAOYSA-N n-(2,3-dihydro-1h-inden-2-yl)-2-(2-fluorophenyl)-n-[(3-fluorophenyl)methyl]benzamide Chemical compound FC1=CC=CC(CN(C2CC3=CC=CC=C3C2)C(=O)C=2C(=CC=CC=2)C=2C(=CC=CC=2)F)=C1 VTCZXXXQDSOQFR-UHFFFAOYSA-N 0.000 claims 1
• YMNWANPXHBMDPU-UHFFFAOYSA-N n-(2,3-dihydro-1h-inden-2-yl)-2-(2-fluorophenyl)-n-[(3-methylphenyl)methyl]benzamide Chemical compound CC1=CC=CC(CN(C2CC3=CC=CC=C3C2)C(=O)C=2C(=CC=CC=2)C=2C(=CC=CC=2)F)=C1 YMNWANPXHBMDPU-UHFFFAOYSA-N 0.000 claims 1
• MSTHBRFPZKTXQH-UHFFFAOYSA-N n-(2,3-dihydro-1h-inden-2-yl)-2-(2-fluorophenyl)-n-[(4-fluorophenyl)methyl]benzamide Chemical compound C1=CC(F)=CC=C1CN(C(=O)C=1C(=CC=CC=1)C=1C(=CC=CC=1)F)C1CC2=CC=CC=C2C1 MSTHBRFPZKTXQH-UHFFFAOYSA-N 0.000 claims 1
• VQQSRWAEKFNPNR-UHFFFAOYSA-N n-(2,3-dihydro-1h-inden-2-yl)-2-(2-fluorophenyl)-n-[(4-methylphenyl)methyl]benzamide Chemical compound C1=CC(C)=CC=C1CN(C(=O)C=1C(=CC=CC=1)C=1C(=CC=CC=1)F)C1CC2=CC=CC=C2C1 VQQSRWAEKFNPNR-UHFFFAOYSA-N 0.000 claims 1
• WIAMKPMPJXUOTK-UHFFFAOYSA-N n-(2,3-dihydro-1h-inden-2-yl)-2-(3-methoxyphenyl)-n-[(3-methylphenyl)methyl]benzamide Chemical compound COC1=CC=CC(C=2C(=CC=CC=2)C(=O)N(CC=2C=C(C)C=CC=2)C2CC3=CC=CC=C3C2)=C1 WIAMKPMPJXUOTK-UHFFFAOYSA-N 0.000 claims 1
• OZZKWHOSRYUNAA-UHFFFAOYSA-N n-(2,3-dihydro-1h-inden-2-yl)-2-(3-methoxyphenyl)-n-[(4-methylphenyl)methyl]benzamide Chemical compound COC1=CC=CC(C=2C(=CC=CC=2)C(=O)N(CC=2C=CC(C)=CC=2)C2CC3=CC=CC=C3C2)=C1 OZZKWHOSRYUNAA-UHFFFAOYSA-N 0.000 claims 1
• PIFHMYUUCHSDLJ-UHFFFAOYSA-N n-(2,3-dihydro-1h-inden-2-yl)-2-(4-methylphenyl)-n-[(2-methylphenyl)methyl]benzamide Chemical compound C1=CC(C)=CC=C1C1=CC=CC=C1C(=O)N(C1CC2=CC=CC=C2C1)CC1=CC=CC=C1C PIFHMYUUCHSDLJ-UHFFFAOYSA-N 0.000 claims 1
• RNJCXZISNCJBDR-UHFFFAOYSA-N n-(2,3-dihydro-1h-inden-2-yl)-2-(4-methylphenyl)-n-[(3-methylphenyl)methyl]benzamide Chemical compound C1=CC(C)=CC=C1C1=CC=CC=C1C(=O)N(C1CC2=CC=CC=C2C1)CC1=CC=CC(C)=C1 RNJCXZISNCJBDR-UHFFFAOYSA-N 0.000 claims 1
• RRWXEYIPOQODHM-UHFFFAOYSA-N n-(2,3-dihydro-1h-inden-2-yl)-2-(4-methylphenyl)-n-[(4-methylphenyl)methyl]benzamide Chemical compound C1=CC(C)=CC=C1CN(C(=O)C=1C(=CC=CC=1)C=1C=CC(C)=CC=1)C1CC2=CC=CC=C2C1 RRWXEYIPOQODHM-UHFFFAOYSA-N 0.000 claims 1
• PJKHIHGUOYAZAN-UHFFFAOYSA-N n-(2,3-dihydro-1h-inden-2-yl)-2-hydroxy-n-[(4-methylphenyl)methyl]naphthalene-1-carboxamide Chemical compound C1=CC(C)=CC=C1CN(C(=O)C=1C2=CC=CC=C2C=CC=1O)C1CC2=CC=CC=C2C1 PJKHIHGUOYAZAN-UHFFFAOYSA-N 0.000 claims 1
• IPPQMCOMOGJUEO-UHFFFAOYSA-N n-(2,3-dihydro-1h-inden-2-yl)-2-methoxy-n-(2-phenylethyl)naphthalene-1-carboxamide Chemical compound COC1=CC=C2C=CC=CC2=C1C(=O)N(C1CC2=CC=CC=C2C1)CCC1=CC=CC=C1 IPPQMCOMOGJUEO-UHFFFAOYSA-N 0.000 claims 1
• DKGLEQYNSYMXMP-UHFFFAOYSA-N n-(2,3-dihydro-1h-inden-2-yl)-2-methoxy-n-[(2-methylphenyl)methyl]naphthalene-1-carboxamide Chemical compound COC1=CC=C2C=CC=CC2=C1C(=O)N(C1CC2=CC=CC=C2C1)CC1=CC=CC=C1C DKGLEQYNSYMXMP-UHFFFAOYSA-N 0.000 claims 1
• DMYAILOXUZNFEV-UHFFFAOYSA-N n-(2,3-dihydro-1h-inden-2-yl)-2-methoxy-n-[(3-methoxyphenyl)methyl]-6-phenylbenzamide Chemical compound COC1=CC=CC(CN(C2CC3=CC=CC=C3C2)C(=O)C=2C(=CC=CC=2OC)C=2C=CC=CC=2)=C1 DMYAILOXUZNFEV-UHFFFAOYSA-N 0.000 claims 1
• SOZFTKFBPZPQBV-UHFFFAOYSA-N n-(2,3-dihydro-1h-inden-2-yl)-2-methoxy-n-[(4-methoxyphenyl)methyl]naphthalene-1-carboxamide Chemical compound C1=CC(OC)=CC=C1CN(C(=O)C=1C2=CC=CC=C2C=CC=1OC)C1CC2=CC=CC=C2C1 SOZFTKFBPZPQBV-UHFFFAOYSA-N 0.000 claims 1
• LUCNNLKTXSJREP-UHFFFAOYSA-N n-(2,3-dihydro-1h-inden-2-yl)-2-methoxy-n-[(4-methylphenyl)methyl]naphthalene-1-carboxamide Chemical compound COC1=CC=C2C=CC=CC2=C1C(=O)N(C1CC2=CC=CC=C2C1)CC1=CC=C(C)C=C1 LUCNNLKTXSJREP-UHFFFAOYSA-N 0.000 claims 1
• VNMUPEUJVMFOEF-UHFFFAOYSA-N n-(2,3-dihydro-1h-inden-2-yl)-2-methyl-6-phenyl-n-(2-phenylethyl)benzamide Chemical compound C=1C=CC=CC=1CCN(C1CC2=CC=CC=C2C1)C(=O)C=1C(C)=CC=CC=1C1=CC=CC=C1 VNMUPEUJVMFOEF-UHFFFAOYSA-N 0.000 claims 1
• VNIGJMXJSWEOKG-UHFFFAOYSA-N n-(2,3-dihydro-1h-inden-2-yl)-2-methyl-n-(2-phenylethyl)naphthalene-1-carboxamide Chemical compound CC1=CC=C2C=CC=CC2=C1C(=O)N(C1CC2=CC=CC=C2C1)CCC1=CC=CC=C1 VNIGJMXJSWEOKG-UHFFFAOYSA-N 0.000 claims 1
• KHWOYXDLKXPJPH-UHFFFAOYSA-N n-(2,3-dihydro-1h-inden-2-yl)-2-methyl-n-[(2-methylphenyl)methyl]-6-phenylbenzamide Chemical compound CC1=CC=CC=C1CN(C(=O)C=1C(=CC=CC=1C)C=1C=CC=CC=1)C1CC2=CC=CC=C2C1 KHWOYXDLKXPJPH-UHFFFAOYSA-N 0.000 claims 1
• QXIHVZFGLTWWPW-UHFFFAOYSA-N n-(2,3-dihydro-1h-inden-2-yl)-2-methyl-n-[(2-methylphenyl)methyl]naphthalene-1-carboxamide Chemical compound CC1=CC=CC=C1CN(C(=O)C=1C2=CC=CC=C2C=CC=1C)C1CC2=CC=CC=C2C1 QXIHVZFGLTWWPW-UHFFFAOYSA-N 0.000 claims 1
• XLESKBUGHZBUIN-UHFFFAOYSA-N n-(2,3-dihydro-1h-inden-2-yl)-2-methyl-n-[(3-methylphenyl)methyl]-6-phenylbenzamide Chemical compound CC1=CC=CC(CN(C2CC3=CC=CC=C3C2)C(=O)C=2C(=CC=CC=2C)C=2C=CC=CC=2)=C1 XLESKBUGHZBUIN-UHFFFAOYSA-N 0.000 claims 1
• HQVFCDCCWAPZCE-UHFFFAOYSA-N n-(2,3-dihydro-1h-inden-2-yl)-2-methyl-n-[(3-methylphenyl)methyl]naphthalene-1-carboxamide Chemical compound CC1=CC=CC(CN(C2CC3=CC=CC=C3C2)C(=O)C=2C3=CC=CC=C3C=CC=2C)=C1 HQVFCDCCWAPZCE-UHFFFAOYSA-N 0.000 claims 1
• DUISPKPTEFJOLH-UHFFFAOYSA-N n-(2,3-dihydro-1h-inden-2-yl)-2-methyl-n-[(4-methylphenyl)methyl]-6-phenylbenzamide Chemical compound C1=CC(C)=CC=C1CN(C(=O)C=1C(=CC=CC=1C)C=1C=CC=CC=1)C1CC2=CC=CC=C2C1 DUISPKPTEFJOLH-UHFFFAOYSA-N 0.000 claims 1
• OUQSATZJYHNIGR-UHFFFAOYSA-N n-(2,3-dihydro-1h-inden-2-yl)-2-methyl-n-[(4-methylphenyl)methyl]naphthalene-1-carboxamide Chemical compound C1=CC(C)=CC=C1CN(C(=O)C=1C2=CC=CC=C2C=CC=1C)C1CC2=CC=CC=C2C1 OUQSATZJYHNIGR-UHFFFAOYSA-N 0.000 claims 1
• ISOSSDQIQUDZOH-UHFFFAOYSA-N n-(2,3-dihydro-1h-inden-2-yl)-5-methoxy-n-[(2-methylphenyl)methyl]-2-phenylbenzamide Chemical compound C=1C=CC=C(C)C=1CN(C1CC2=CC=CC=C2C1)C(=O)C1=CC(OC)=CC=C1C1=CC=CC=C1 ISOSSDQIQUDZOH-UHFFFAOYSA-N 0.000 claims 1
• QPFMSABCGBELDC-UHFFFAOYSA-N n-(2,3-dihydro-1h-inden-2-yl)-5-methoxy-n-[(3-methoxyphenyl)methyl]-2-(5-methylthiophen-2-yl)benzamide Chemical compound COC1=CC=CC(CN(C2CC3=CC=CC=C3C2)C(=O)C=2C(=CC=C(OC)C=2)C=2SC(C)=CC=2)=C1 QPFMSABCGBELDC-UHFFFAOYSA-N 0.000 claims 1
• YGUVKNSJMSWCQA-UHFFFAOYSA-N n-(2,3-dihydro-1h-inden-2-yl)-5-methoxy-n-[(3-methoxyphenyl)methyl]-2-phenylbenzamide Chemical compound COC1=CC=CC(CN(C2CC3=CC=CC=C3C2)C(=O)C=2C(=CC=C(OC)C=2)C=2C=CC=CC=2)=C1 YGUVKNSJMSWCQA-UHFFFAOYSA-N 0.000 claims 1
• CHEDUXCSRIWMTM-UHFFFAOYSA-N n-(2,3-dihydro-1h-inden-2-yl)-5-methoxy-n-[(3-methoxyphenyl)methyl]-2-thiophen-3-ylbenzamide Chemical compound COC1=CC=CC(CN(C2CC3=CC=CC=C3C2)C(=O)C=2C(=CC=C(OC)C=2)C2=CSC=C2)=C1 CHEDUXCSRIWMTM-UHFFFAOYSA-N 0.000 claims 1
• UHSKYZXAUCDMQE-UHFFFAOYSA-N n-(2,3-dihydro-1h-inden-2-yl)-5-methoxy-n-[(3-methylphenyl)methyl]-2-phenylbenzamide Chemical compound C=1C=CC(C)=CC=1CN(C1CC2=CC=CC=C2C1)C(=O)C1=CC(OC)=CC=C1C1=CC=CC=C1 UHSKYZXAUCDMQE-UHFFFAOYSA-N 0.000 claims 1
• INCDGTYGBJZQMJ-UHFFFAOYSA-N n-(2,3-dihydro-1h-inden-2-yl)-5-methoxy-n-[(4-methylphenyl)methyl]-2-phenylbenzamide Chemical compound C=1C=C(C)C=CC=1CN(C1CC2=CC=CC=C2C1)C(=O)C1=CC(OC)=CC=C1C1=CC=CC=C1 INCDGTYGBJZQMJ-UHFFFAOYSA-N 0.000 claims 1
• OMTACZSLWIFNHD-UHFFFAOYSA-N n-(2,3-dihydro-1h-inden-2-yl)-n-(naphthalen-2-ylmethyl)-2-thiophen-3-ylbenzamide Chemical compound C=1C=C2C=CC=CC2=CC=1CN(C1CC2=CC=CC=C2C1)C(=O)C1=CC=CC=C1C=1C=CSC=1 OMTACZSLWIFNHD-UHFFFAOYSA-N 0.000 claims 1
• PKIHNMFXTCUSQR-UHFFFAOYSA-N n-(2,3-dihydro-1h-inden-2-yl)-n-[(2-fluorophenyl)methyl]-2-(4-methylphenyl)benzamide Chemical compound C1=CC(C)=CC=C1C1=CC=CC=C1C(=O)N(C1CC2=CC=CC=C2C1)CC1=CC=CC=C1F PKIHNMFXTCUSQR-UHFFFAOYSA-N 0.000 claims 1
• YAKMAHBUAMQTFO-UHFFFAOYSA-N n-(2,3-dihydro-1h-inden-2-yl)-n-[(2-fluorophenyl)methyl]-2-methyl-6-phenylbenzamide Chemical compound C=1C=CC=C(F)C=1CN(C1CC2=CC=CC=C2C1)C(=O)C=1C(C)=CC=CC=1C1=CC=CC=C1 YAKMAHBUAMQTFO-UHFFFAOYSA-N 0.000 claims 1
• CZNCRUXJXDUIPP-UHFFFAOYSA-N n-(2,3-dihydro-1h-inden-2-yl)-n-[(2-fluorophenyl)methyl]-2-methylnaphthalene-1-carboxamide Chemical compound CC1=CC=C2C=CC=CC2=C1C(=O)N(C1CC2=CC=CC=C2C1)CC1=CC=CC=C1F CZNCRUXJXDUIPP-UHFFFAOYSA-N 0.000 claims 1
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