JP2005500400A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2005500400A5 JP2005500400A5 JP2003523200A JP2003523200A JP2005500400A5 JP 2005500400 A5 JP2005500400 A5 JP 2005500400A5 JP 2003523200 A JP2003523200 A JP 2003523200A JP 2003523200 A JP2003523200 A JP 2003523200A JP 2005500400 A5 JP2005500400 A5 JP 2005500400A5
- Authority
- JP
- Japan
- Prior art keywords
- phenyl
- amino
- chloro
- alkyl
- methylphenyl
- 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.)
- Granted
Links
- 125000001424 substituent group Chemical group 0.000 claims 74
- 125000000753 cycloalkyl group Chemical group 0.000 claims 52
- 150000001336 alkenes Chemical group 0.000 claims 49
- -1 phenylamino-2′-methylbenzophenone Chemical compound 0.000 claims 44
- 125000000217 alkyl group Chemical group 0.000 claims 30
- 125000000623 heterocyclic group Chemical group 0.000 claims 29
- 150000001875 compounds Chemical class 0.000 claims 26
- 229910052739 hydrogen Inorganic materials 0.000 claims 26
- 239000001257 hydrogen Substances 0.000 claims 26
- 229910052736 halogen Inorganic materials 0.000 claims 25
- 150000002367 halogens Chemical class 0.000 claims 25
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 19
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 18
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims 15
- 150000002431 hydrogen Chemical class 0.000 claims 15
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 14
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 14
- 125000004093 cyano group Chemical group *C#N 0.000 claims 13
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 10
- 125000000304 alkynyl group Chemical group 0.000 claims 9
- OSDBJMYIUDLIRI-UHFFFAOYSA-N oxo-[[1-[[4-[[4-(oxoazaniumylmethylidene)pyridin-1-yl]methoxy]cyclohexyl]oxymethyl]pyridin-4-ylidene]methyl]azanium;dichloride Chemical compound [Cl-].[Cl-].C1=CC(=C[NH+]=O)C=CN1COC1CCC(OCN2C=CC(=C[NH+]=O)C=C2)CC1 OSDBJMYIUDLIRI-UHFFFAOYSA-N 0.000 claims 9
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims 8
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 8
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 8
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 8
- 125000002950 monocyclic group Chemical group 0.000 claims 8
- 125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims 7
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 7
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 6
- 125000004414 alkyl thio group Chemical group 0.000 claims 5
- HVAUUPRFYPCOCA-AREMUKBSSA-N 2-O-acetyl-1-O-hexadecyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCCOC[C@@H](OC(C)=O)COP([O-])(=O)OCC[N+](C)(C)C HVAUUPRFYPCOCA-AREMUKBSSA-N 0.000 claims 4
- 108010003541 Platelet Activating Factor Proteins 0.000 claims 4
- 125000003545 alkoxy group Chemical group 0.000 claims 4
- 125000003282 alkyl amino group Chemical group 0.000 claims 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 4
- CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 claims 4
- 229910052760 oxygen Inorganic materials 0.000 claims 4
- 239000001301 oxygen Substances 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 3
- 150000001450 anions Chemical class 0.000 claims 3
- 125000004429 atom Chemical group 0.000 claims 3
- KWEDUNSJJZVRKR-UHFFFAOYSA-N carbononitridic azide Chemical compound [N-]=[N+]=NC#N KWEDUNSJJZVRKR-UHFFFAOYSA-N 0.000 claims 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 3
- 125000001072 heteroaryl group Chemical group 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 238000006467 substitution reaction Methods 0.000 claims 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 3
- 125000005208 trialkylammonium group Chemical group 0.000 claims 3
- 125000006526 (C1-C2) alkyl group Chemical group 0.000 claims 2
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 2
- 125000006593 (C2-C3) alkynyl group Chemical group 0.000 claims 2
- RTAPDZBZLSXHQQ-UHFFFAOYSA-N 8-methyl-3,7-dihydropurine-2,6-dione Chemical class N1C(=O)NC(=O)C2=C1N=C(C)N2 RTAPDZBZLSXHQQ-UHFFFAOYSA-N 0.000 claims 2
- 208000030507 AIDS Diseases 0.000 claims 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 2
- 208000002874 Acne Vulgaris Diseases 0.000 claims 2
- 201000001320 Atherosclerosis Diseases 0.000 claims 2
- 208000011231 Crohn disease Diseases 0.000 claims 2
- 201000004624 Dermatitis Diseases 0.000 claims 2
- 206010012438 Dermatitis atopic Diseases 0.000 claims 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 2
- 201000005569 Gout Diseases 0.000 claims 2
- 206010020751 Hypersensitivity Diseases 0.000 claims 2
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 2
- CMWTZPSULFXXJA-UHFFFAOYSA-N Naproxen Natural products C1=C(C(C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-UHFFFAOYSA-N 0.000 claims 2
- 208000001132 Osteoporosis Diseases 0.000 claims 2
- 201000004681 Psoriasis Diseases 0.000 claims 2
- 206010040070 Septic Shock Diseases 0.000 claims 2
- 206010046851 Uveitis Diseases 0.000 claims 2
- 229930003316 Vitamin D Natural products 0.000 claims 2
- QYSXJUFSXHHAJI-XFEUOLMDSA-N Vitamin D3 Natural products C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CCCC(C)C)=C/C=C1\C[C@@H](O)CCC1=C QYSXJUFSXHHAJI-XFEUOLMDSA-N 0.000 claims 2
- 229940022663 acetate Drugs 0.000 claims 2
- 206010000496 acne Diseases 0.000 claims 2
- 239000004480 active ingredient Substances 0.000 claims 2
- 230000007815 allergy Effects 0.000 claims 2
- 239000005557 antagonist Substances 0.000 claims 2
- 239000003529 anticholesteremic agent Substances 0.000 claims 2
- 229940127226 anticholesterol agent Drugs 0.000 claims 2
- 229940125715 antihistaminic agent Drugs 0.000 claims 2
- 239000000739 antihistaminic agent Substances 0.000 claims 2
- 206010003246 arthritis Diseases 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 208000006673 asthma Diseases 0.000 claims 2
- 201000008937 atopic dermatitis Diseases 0.000 claims 2
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 claims 2
- 239000000812 cholinergic antagonist Substances 0.000 claims 2
- 230000001684 chronic effect Effects 0.000 claims 2
- 229940111134 coxibs Drugs 0.000 claims 2
- 239000003255 cyclooxygenase 2 inhibitor Substances 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 239000003862 glucocorticoid Substances 0.000 claims 2
- 150000004677 hydrates Chemical class 0.000 claims 2
- 229960000905 indomethacin Drugs 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- 229960002009 naproxen Drugs 0.000 claims 2
- CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical compound C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 claims 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims 2
- 230000002062 proliferating effect Effects 0.000 claims 2
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 2
- 150000003873 salicylate salts Chemical class 0.000 claims 2
- 230000036303 septic shock Effects 0.000 claims 2
- 239000012453 solvate Substances 0.000 claims 2
- GECHUMIMRBOMGK-UHFFFAOYSA-N sulfapyridine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=CC=CC=N1 GECHUMIMRBOMGK-UHFFFAOYSA-N 0.000 claims 2
- 229960002211 sulfapyridine Drugs 0.000 claims 2
- 229940037128 systemic glucocorticoids Drugs 0.000 claims 2
- 235000019166 vitamin D Nutrition 0.000 claims 2
- 239000011710 vitamin D Substances 0.000 claims 2
- 150000003710 vitamin D derivatives Chemical class 0.000 claims 2
- 229940046008 vitamin d Drugs 0.000 claims 2
- LJRDOKAZOAKLDU-UDXJMMFXSA-N (2s,3s,4r,5r,6r)-5-amino-2-(aminomethyl)-6-[(2r,3s,4r,5s)-5-[(1r,2r,3s,5r,6s)-3,5-diamino-2-[(2s,3r,4r,5s,6r)-3-amino-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-hydroxycyclohexyl]oxy-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]oxyoxane-3,4-diol;sulfuric ac Chemical compound OS(O)(=O)=O.N[C@@H]1[C@@H](O)[C@H](O)[C@H](CN)O[C@@H]1O[C@H]1[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](N)C[C@@H](N)[C@@H]2O)O[C@@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)N)O[C@@H]1CO LJRDOKAZOAKLDU-UDXJMMFXSA-N 0.000 claims 1
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims 1
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
- KTWGOKKSCUEMKS-JLHYYAGUSA-N (e)-3-[2-[3-chloro-4-(2-methylbenzoyl)anilino]phenyl]prop-2-enoic acid Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1\C=C\C(O)=O KTWGOKKSCUEMKS-JLHYYAGUSA-N 0.000 claims 1
- XPYLTEPNMPTZHK-FMIVXFBMSA-N 1-[(e)-3-[2-[3-chloro-4-(2-methylbenzoyl)anilino]phenyl]prop-2-enyl]-3-cyclohexylurea Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1\C=C\CNC(=O)NC1CCCCC1 XPYLTEPNMPTZHK-FMIVXFBMSA-N 0.000 claims 1
- RFNPZCSRTULLJK-DHZHZOJOSA-N 1-[(e)-3-[2-[3-chloro-4-(2-methylbenzoyl)anilino]phenyl]prop-2-enyl]-3-ethylurea Chemical compound CCNC(=O)NC\C=C\C1=CC=CC=C1NC(C=C1Cl)=CC=C1C(=O)C1=CC=CC=C1C RFNPZCSRTULLJK-DHZHZOJOSA-N 0.000 claims 1
- RZWCUNNVHPRHEE-UHFFFAOYSA-N 1-[2-[2-[3-chloro-4-(2-methylbenzoyl)anilino]phenyl]ethyl]piperidine-2,6-dione Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1CCN1C(=O)CCCC1=O RZWCUNNVHPRHEE-UHFFFAOYSA-N 0.000 claims 1
- JFPGKEOODBKLDU-UHFFFAOYSA-N 1-[2-[3-chloro-4-(2-methylbenzoyl)anilino]phenyl]propan-2-yl acetate Chemical compound CC(=O)OC(C)CC1=CC=CC=C1NC(C=C1Cl)=CC=C1C(=O)C1=CC=CC=C1C JFPGKEOODBKLDU-UHFFFAOYSA-N 0.000 claims 1
- BMJKBOXGLHNRMG-UHFFFAOYSA-N 1-[2-[3-chloro-4-(2-methylbenzoyl)anilino]phenyl]pyrrolidine-2,5-dione Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1N1C(=O)CCC1=O BMJKBOXGLHNRMG-UHFFFAOYSA-N 0.000 claims 1
- QUTJEJGGKZLXMV-UHFFFAOYSA-N 1-[2-[[5-bromo-2-[3-chloro-4-(2-methylbenzoyl)anilino]phenyl]methoxy]ethyl]imidazolidine-2,4,5-trione Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=C(Br)C=C1COCCN1C(=O)C(=O)NC1=O QUTJEJGGKZLXMV-UHFFFAOYSA-N 0.000 claims 1
- YMROMRJRSLUTOM-UHFFFAOYSA-N 1-[2-[[5-bromo-2-[3-chloro-4-(2-methylbenzoyl)anilino]phenyl]methoxy]ethyl]pyrrolidine-2,5-dione Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=C(Br)C=C1COCCN1C(=O)CCC1=O YMROMRJRSLUTOM-UHFFFAOYSA-N 0.000 claims 1
- WFQHSZANBLMBPZ-UHFFFAOYSA-N 1-[3-[2-[2-[3-chloro-4-(2-methylbenzoyl)anilino]phenyl]ethylamino]propyl]pyrrolidin-2-one Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1CCNCCCN1C(=O)CCC1 WFQHSZANBLMBPZ-UHFFFAOYSA-N 0.000 claims 1
- RYSROKNDIDHZJI-FMIVXFBMSA-N 1-tert-butyl-3-[(e)-3-[2-[3-chloro-4-(2-methylbenzoyl)anilino]phenyl]prop-2-enyl]thiourea Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1\C=C\CNC(=S)NC(C)(C)C RYSROKNDIDHZJI-FMIVXFBMSA-N 0.000 claims 1
- QZVRGOQYKYFZGD-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethyl 4-[2-[3-chloro-4-(2-methylbenzoyl)anilino]anilino]-4-oxobutanoate Chemical compound COCCOCCOC(=O)CCC(=O)NC1=CC=CC=C1NC(C=C1Cl)=CC=C1C(=O)C1=CC=CC=C1C QZVRGOQYKYFZGD-UHFFFAOYSA-N 0.000 claims 1
- CJPJIIPRRZLRNR-JXMROGBWSA-N 2-[1-[(e)-3-[2-[3-chloro-4-(2-methylbenzoyl)anilino]phenyl]prop-2-enyl]piperidin-4-yl]ethyl acetate Chemical compound C1CC(CCOC(=O)C)CCN1C\C=C\C1=CC=CC=C1NC(C=C1Cl)=CC=C1C(=O)C1=CC=CC=C1C CJPJIIPRRZLRNR-JXMROGBWSA-N 0.000 claims 1
- KFKXIYKEYLVBBL-DHZHZOJOSA-N 2-[2-acetyloxyethyl-[(e)-3-[2-[3-chloro-4-(2-methylbenzoyl)anilino]phenyl]prop-2-enyl]amino]ethyl acetate Chemical compound CC(=O)OCCN(CCOC(C)=O)C\C=C\C1=CC=CC=C1NC(C=C1Cl)=CC=C1C(=O)C1=CC=CC=C1C KFKXIYKEYLVBBL-DHZHZOJOSA-N 0.000 claims 1
- KOSFPIUIERYHRN-UHFFFAOYSA-N 2-[[2-[3-chloro-4-(2-methylbenzoyl)anilino]phenyl]methyl]isoindole-1,3-dione Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1CN1C(=O)C2=CC=CC=C2C1=O KOSFPIUIERYHRN-UHFFFAOYSA-N 0.000 claims 1
- CSZLAGIWFMBBMI-UHFFFAOYSA-N 2-[[5-bromo-2-[3-chloro-4-(2-methylbenzoyl)anilino]phenyl]methoxy]ethyl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OCCOCC1=CC(Br)=CC=C1NC(C=C1Cl)=CC=C1C(=O)C1=CC=CC=C1C CSZLAGIWFMBBMI-UHFFFAOYSA-N 0.000 claims 1
- PXHPHZOZEUGBMZ-UHFFFAOYSA-N 2-phenylethyl n-[2-[3-chloro-4-(2-methylbenzoyl)anilino]phenyl]carbamate Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1NC(=O)OCCC1=CC=CC=C1 PXHPHZOZEUGBMZ-UHFFFAOYSA-N 0.000 claims 1
- FEPBWGFYSIXPHS-UHFFFAOYSA-N 3-[2-[2-[3-chloro-4-(2-methylbenzoyl)anilino]phenyl]ethyl]-1-methylimidazolidine-2,4-dione Chemical compound O=C1N(C)CC(=O)N1CCC1=CC=CC=C1NC(C=C1Cl)=CC=C1C(=O)C1=CC=CC=C1C FEPBWGFYSIXPHS-UHFFFAOYSA-N 0.000 claims 1
- LXSQYLFYLSVYHI-UHFFFAOYSA-N 3-[2-[[5-bromo-2-[3-chloro-4-(2-methylbenzoyl)anilino]phenyl]methoxy]ethyl]-1-methylimidazolidine-2,4-dione Chemical compound O=C1N(C)CC(=O)N1CCOCC1=CC(Br)=CC=C1NC(C=C1Cl)=CC=C1C(=O)C1=CC=CC=C1C LXSQYLFYLSVYHI-UHFFFAOYSA-N 0.000 claims 1
- NNZZVRROPKCPGG-UHFFFAOYSA-N 3-[2-[[5-bromo-2-[3-chloro-4-(2-methylbenzoyl)anilino]phenyl]methoxy]ethyl]imidazolidine-2,4-dione Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=C(Br)C=C1COCCN1C(=O)NCC1=O NNZZVRROPKCPGG-UHFFFAOYSA-N 0.000 claims 1
- GXFWGLFVQPHTNC-UHFFFAOYSA-N 4-[2-[2-[3-chloro-4-(2-methylbenzoyl)anilino]phenyl]ethoxy]-4-oxobutanoic acid Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1CCOC(=O)CCC(O)=O GXFWGLFVQPHTNC-UHFFFAOYSA-N 0.000 claims 1
- PPXMCTKVIGKWKP-UHFFFAOYSA-N 4-[2-[2-[3-chloro-4-(2-methylbenzoyl)anilino]phenyl]ethyl]morpholine-3,5-dione Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1CCN1C(=O)COCC1=O PPXMCTKVIGKWKP-UHFFFAOYSA-N 0.000 claims 1
- XELONKVQFGEAJV-UHFFFAOYSA-N 4-[2-[[5-bromo-2-[3-chloro-4-(2-methylbenzoyl)anilino]phenyl]methoxy]ethyl]morpholine-3,5-dione Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=C(Br)C=C1COCCN1C(=O)COCC1=O XELONKVQFGEAJV-UHFFFAOYSA-N 0.000 claims 1
- YOHHMUHECKKHSO-UHFFFAOYSA-N 6-[[4-[2-[3-chloro-4-(2-methylbenzoyl)anilino]anilino]-4-oxobutanoyl]amino]hexyl diethyl phosphate Chemical compound CCOP(=O)(OCC)OCCCCCCNC(=O)CCC(=O)NC1=CC=CC=C1NC(C=C1Cl)=CC=C1C(=O)C1=CC=CC=C1C YOHHMUHECKKHSO-UHFFFAOYSA-N 0.000 claims 1
- MSNYPHBTGPIMNJ-UHFFFAOYSA-N 6-chloro-4-[2-[2-(hydroxymethyl)anilino]phenyl]-6-methylcyclohexa-2,4-diene-1-carbaldehyde Chemical compound ClC1(C(C=CC(=C1)C1=C(C=CC=C1)NC1=C(C=CC=C1)CO)C=O)C MSNYPHBTGPIMNJ-UHFFFAOYSA-N 0.000 claims 1
- DHMQDGOQFOQNFH-UHFFFAOYSA-M Aminoacetate Chemical compound NCC([O-])=O DHMQDGOQFOQNFH-UHFFFAOYSA-M 0.000 claims 1
- YCGVIPPYKJOKMZ-UHFFFAOYSA-N BrC=1C=CC(=C(COCCOCCOCCC2=CC=C(C=C2)C)C1)NC1=CC(=C(C=C1)C(=O)C1=C(C=CC=C1)C)Cl Chemical compound BrC=1C=CC(=C(COCCOCCOCCC2=CC=C(C=C2)C)C1)NC1=CC(=C(C=C1)C(=O)C1=C(C=CC=C1)C)Cl YCGVIPPYKJOKMZ-UHFFFAOYSA-N 0.000 claims 1
- 229940121948 Muscarinic receptor antagonist Drugs 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- ODLLIVVLGBEBBU-ISILISOKSA-N [(3s,4r)-4-acetyloxy-1-[2-[[5-bromo-2-[3-chloro-4-(2-methylbenzoyl)anilino]phenyl]methoxy]ethyl]-2,5-dioxopyrrolidin-3-yl] acetate Chemical compound O=C1[C@@H](OC(=O)C)[C@@H](OC(C)=O)C(=O)N1CCOCC1=CC(Br)=CC=C1NC(C=C1Cl)=CC=C1C(=O)C1=CC=CC=C1C ODLLIVVLGBEBBU-ISILISOKSA-N 0.000 claims 1
- TVDGPILBCCYQDT-UHFFFAOYSA-N [2-[2-[3-chloro-4-(2-methylbenzoyl)anilino]anilino]-2-oxoethyl] acetate Chemical compound CC(=O)OCC(=O)NC1=CC=CC=C1NC(C=C1Cl)=CC=C1C(=O)C1=CC=CC=C1C TVDGPILBCCYQDT-UHFFFAOYSA-N 0.000 claims 1
- ZFTRXOHRPWHONP-UHFFFAOYSA-N [2-[3-chloro-4-(2-methylbenzoyl)anilino]phenyl]methylphosphonic acid Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1CP(O)(O)=O ZFTRXOHRPWHONP-UHFFFAOYSA-N 0.000 claims 1
- QGROFRDWLVHLJJ-UHFFFAOYSA-N [2-[[2-[3-chloro-4-(2-methylbenzoyl)anilino]phenyl]methylamino]-2-oxoethyl]phosphonic acid Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1CNC(=O)CP(O)(O)=O QGROFRDWLVHLJJ-UHFFFAOYSA-N 0.000 claims 1
- COBTVLLYFAQVRY-UHFFFAOYSA-N [2-chloro-4-[2-(2-hydroxyethoxymethyl)anilino]phenyl]-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1COCCO COBTVLLYFAQVRY-UHFFFAOYSA-N 0.000 claims 1
- AQEXUXIKCRBBTI-UHFFFAOYSA-N [2-chloro-4-[2-(2-hydroxyethyl)anilino]phenyl]-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1CCO AQEXUXIKCRBBTI-UHFFFAOYSA-N 0.000 claims 1
- LWZGMWIWPHBAKE-UHFFFAOYSA-N [2-chloro-4-[2-(2-hydroxypropyl)anilino]phenyl]-(2-methylphenyl)methanone Chemical compound CC(O)CC1=CC=CC=C1NC(C=C1Cl)=CC=C1C(=O)C1=CC=CC=C1C LWZGMWIWPHBAKE-UHFFFAOYSA-N 0.000 claims 1
- FKAKZFHOHZVOLC-UHFFFAOYSA-N [2-chloro-4-[2-(2-iodoethoxymethyl)anilino]phenyl]-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1COCCI FKAKZFHOHZVOLC-UHFFFAOYSA-N 0.000 claims 1
- NDKXFNRRNWLTOB-UHFFFAOYSA-N [2-chloro-4-[2-(2-morpholin-4-ylethyl)anilino]phenyl]-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1CCN1CCOCC1 NDKXFNRRNWLTOB-UHFFFAOYSA-N 0.000 claims 1
- XFFBBCSESUJDNO-UHFFFAOYSA-N [2-chloro-4-[2-(3,3,3-trifluoropropoxymethyl)anilino]phenyl]-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1COCCC(F)(F)F XFFBBCSESUJDNO-UHFFFAOYSA-N 0.000 claims 1
- QJNDYVOPQXQBNY-UHFFFAOYSA-N [2-chloro-4-[2-(3-hydroxypropoxy)anilino]phenyl]-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1OCCCO QJNDYVOPQXQBNY-UHFFFAOYSA-N 0.000 claims 1
- RRSFHQAHCUJBHL-UHFFFAOYSA-N [2-chloro-4-[2-(3-hydroxypropoxymethyl)anilino]phenyl]-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1COCCCO RRSFHQAHCUJBHL-UHFFFAOYSA-N 0.000 claims 1
- UQOGBJHKQSJAOQ-UHFFFAOYSA-N [2-chloro-4-[2-(3-hydroxypropyl)anilino]phenyl]-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1CCCO UQOGBJHKQSJAOQ-UHFFFAOYSA-N 0.000 claims 1
- WRXKBZQHBPVHRZ-UHFFFAOYSA-N [2-chloro-4-[2-(3-morpholin-4-ylpropoxy)anilino]phenyl]-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1OCCCN1CCOCC1 WRXKBZQHBPVHRZ-UHFFFAOYSA-N 0.000 claims 1
- OXQJRCMVWRSKIU-UHFFFAOYSA-N [2-chloro-4-[2-(diethoxyphosphorylmethyl)anilino]phenyl]-(2-methylphenyl)methanone Chemical compound CCOP(=O)(OCC)CC1=CC=CC=C1NC(C=C1Cl)=CC=C1C(=O)C1=CC=CC=C1C OXQJRCMVWRSKIU-UHFFFAOYSA-N 0.000 claims 1
- PVYCUEDTOJBESW-UHFFFAOYSA-N [2-chloro-4-[2-(difluoromethyl)anilino]phenyl]-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1C(F)F PVYCUEDTOJBESW-UHFFFAOYSA-N 0.000 claims 1
- NTOZLMJJFHITTN-RMKNXTFCSA-N [2-chloro-4-[2-[(e)-3-(2,3-dihydroxypropoxy)prop-1-enyl]anilino]phenyl]-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1\C=C\COCC(O)CO NTOZLMJJFHITTN-RMKNXTFCSA-N 0.000 claims 1
- UTVKSMGDMZRRBR-DHZHZOJOSA-N [2-chloro-4-[2-[(e)-3-[(2,2-dimethyl-1,3-dioxolan-4-yl)methoxy]prop-1-enyl]anilino]phenyl]-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1\C=C\COCC1OC(C)(C)OC1 UTVKSMGDMZRRBR-DHZHZOJOSA-N 0.000 claims 1
- ZJTOJZDPLYKOAU-RMKNXTFCSA-N [2-chloro-4-[2-[(e)-3-[4-(2-hydroxyethyl)piperidin-1-yl]prop-1-enyl]anilino]phenyl]-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1\C=C\CN1CCC(CCO)CC1 ZJTOJZDPLYKOAU-RMKNXTFCSA-N 0.000 claims 1
- JFZBWOMYLXOISH-RDIUEAQDSA-N [2-chloro-4-[2-[(e)-3-[[(2r,3s,4r,5r)-3,4-dihydroxy-5-methoxyoxolan-2-yl]methoxy]prop-1-enyl]anilino]phenyl]-(2-methylphenyl)methanone Chemical compound O[C@H]1[C@@H](O)[C@H](OC)O[C@@H]1COC\C=C\C1=CC=CC=C1NC(C=C1Cl)=CC=C1C(=O)C1=CC=CC=C1C JFZBWOMYLXOISH-RDIUEAQDSA-N 0.000 claims 1
- NUCUIYGJDKXZST-CCEZHUSRSA-N [2-chloro-4-[2-[(e)-3-hydroxy-3-methylbut-1-enyl]anilino]phenyl]-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1\C=C\C(C)(C)O NUCUIYGJDKXZST-CCEZHUSRSA-N 0.000 claims 1
- UDMUMCMGVXOTKJ-RMKNXTFCSA-N [2-chloro-4-[2-[(e)-3-hydroxyprop-1-enyl]anilino]phenyl]-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1\C=C\CO UDMUMCMGVXOTKJ-RMKNXTFCSA-N 0.000 claims 1
- KTMQZZJSCFPLMM-RMKNXTFCSA-N [2-chloro-4-[2-[(e)-3-morpholin-4-ylprop-1-enyl]anilino]phenyl]-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1\C=C\CN1CCOCC1 KTMQZZJSCFPLMM-RMKNXTFCSA-N 0.000 claims 1
- SVRDBGWQNMQEOR-UXBLZVDNSA-N [2-chloro-4-[2-[(e)-4-hydroxybut-1-enyl]anilino]phenyl]-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1\C=C\CCO SVRDBGWQNMQEOR-UXBLZVDNSA-N 0.000 claims 1
- KSPIAUMASCIUMD-UHFFFAOYSA-N [2-chloro-4-[2-[2-(2,3-dihydroxypropylamino)ethyl]anilino]phenyl]-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1CCNCC(O)CO KSPIAUMASCIUMD-UHFFFAOYSA-N 0.000 claims 1
- PDIPQSUMQLMPMJ-UHFFFAOYSA-N [2-chloro-4-[2-[2-(2-hydroxyethoxy)ethoxymethyl]anilino]phenyl]-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1COCCOCCO PDIPQSUMQLMPMJ-UHFFFAOYSA-N 0.000 claims 1
- NTLRZVOLQGREDX-UHFFFAOYSA-N [2-chloro-4-[2-[2-(2-methoxyethylamino)ethyl]anilino]phenyl]-(2-methylphenyl)methanone Chemical compound COCCNCCC1=CC=CC=C1NC(C=C1Cl)=CC=C1C(=O)C1=CC=CC=C1C NTLRZVOLQGREDX-UHFFFAOYSA-N 0.000 claims 1
- RCCQNKHHDLILAT-UHFFFAOYSA-N [2-chloro-4-[2-[2-(3-morpholin-4-ylpropylamino)ethyl]anilino]phenyl]-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1CCNCCCN1CCOCC1 RCCQNKHHDLILAT-UHFFFAOYSA-N 0.000 claims 1
- DJNOKUPKSWCZCS-UHFFFAOYSA-N [2-chloro-4-[2-[2-(4-methylpiperazin-1-yl)ethyl]anilino]phenyl]-(2-methylphenyl)methanone Chemical compound C1CN(C)CCN1CCC1=CC=CC=C1NC(C=C1Cl)=CC=C1C(=O)C1=CC=CC=C1C DJNOKUPKSWCZCS-UHFFFAOYSA-N 0.000 claims 1
- ZYWGKZMKBOUKDL-UHFFFAOYSA-N [2-chloro-4-[2-[2-(oxan-2-yloxy)ethoxymethyl]anilino]phenyl]-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1COCCOC1OCCCC1 ZYWGKZMKBOUKDL-UHFFFAOYSA-N 0.000 claims 1
- WVEAJVSHVDREKJ-UHFFFAOYSA-N [2-chloro-4-[2-[2-(oxan-2-yloxy)ethyl]anilino]phenyl]-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1CCOC1OCCCC1 WVEAJVSHVDREKJ-UHFFFAOYSA-N 0.000 claims 1
- DKEPJJPFNUZKIO-UHFFFAOYSA-N [2-chloro-4-[2-[2-(oxolan-2-ylmethylamino)ethyl]anilino]phenyl]-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1CCNCC1OCCC1 DKEPJJPFNUZKIO-UHFFFAOYSA-N 0.000 claims 1
- JBVVZYRHOIGKAQ-UHFFFAOYSA-N [2-chloro-4-[2-[2-[(2,2-dimethyl-1,3-dioxolan-4-yl)methylamino]ethyl]anilino]phenyl]-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1CCNCC1OC(C)(C)OC1 JBVVZYRHOIGKAQ-UHFFFAOYSA-N 0.000 claims 1
- RKZMCLZKKWICRJ-UHFFFAOYSA-N [2-chloro-4-[2-[2-[2-(2-hydroxyethoxy)ethoxy]ethoxymethyl]anilino]phenyl]-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1COCCOCCOCCO RKZMCLZKKWICRJ-UHFFFAOYSA-N 0.000 claims 1
- UKXMOHJCRFYPKZ-UHFFFAOYSA-N [2-chloro-4-[2-[2-[2-(dimethylamino)ethylamino]ethyl]anilino]phenyl]-(2-methylphenyl)methanone Chemical compound CN(C)CCNCCC1=CC=CC=C1NC(C=C1Cl)=CC=C1C(=O)C1=CC=CC=C1C UKXMOHJCRFYPKZ-UHFFFAOYSA-N 0.000 claims 1
- VVMJQNVGIRFNNN-UHFFFAOYSA-N [2-chloro-4-[2-[2-[2-(oxan-2-yloxy)ethoxy]ethoxymethyl]anilino]phenyl]-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1COCCOCCOC1OCCCC1 VVMJQNVGIRFNNN-UHFFFAOYSA-N 0.000 claims 1
- HEIWFPMTWKROQV-UHFFFAOYSA-N [2-chloro-4-[2-[2-[2-[2-(oxan-2-yloxy)ethoxy]ethoxy]ethoxymethyl]anilino]phenyl]-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1COCCOCCOCCOC1OCCCC1 HEIWFPMTWKROQV-UHFFFAOYSA-N 0.000 claims 1
- UJFMINQOZPVJLO-UHFFFAOYSA-N [2-chloro-4-[2-[2-[4-(2-methoxyethyl)piperazin-1-yl]ethyl]anilino]phenyl]-(2-methylphenyl)methanone Chemical compound C1CN(CCOC)CCN1CCC1=CC=CC=C1NC(C=C1Cl)=CC=C1C(=O)C1=CC=CC=C1C UJFMINQOZPVJLO-UHFFFAOYSA-N 0.000 claims 1
- CPTGOZQAFRERIV-UHFFFAOYSA-N [2-chloro-4-[2-[2-[methyl(oxolan-2-ylmethyl)amino]ethyl]anilino]phenyl]-(2-methylphenyl)methanone Chemical compound C1CCOC1CN(C)CCC1=CC=CC=C1NC(C=C1Cl)=CC=C1C(=O)C1=CC=CC=C1C CPTGOZQAFRERIV-UHFFFAOYSA-N 0.000 claims 1
- PKCIXQGQZBYYTQ-UHFFFAOYSA-N [2-chloro-4-[2-[3-(oxan-2-yloxy)propoxy]anilino]phenyl]-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1OCCCOC1OCCCC1 PKCIXQGQZBYYTQ-UHFFFAOYSA-N 0.000 claims 1
- UUWUJULUPQOGHD-UHFFFAOYSA-N [2-chloro-4-[2-[3-(oxan-2-yloxy)propoxymethyl]anilino]phenyl]-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1COCCCOC1OCCCC1 UUWUJULUPQOGHD-UHFFFAOYSA-N 0.000 claims 1
- XYINPYRVKHCBQB-UHFFFAOYSA-N [4-[2-(aminomethyl)anilino]-2-chlorophenyl]-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1CN XYINPYRVKHCBQB-UHFFFAOYSA-N 0.000 claims 1
- WXVGFWDXCCYEPR-RMKNXTFCSA-N [4-[2-[(e)-3-[bis(2-hydroxyethyl)amino]prop-1-enyl]anilino]-2-chlorophenyl]-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1\C=C\CN(CCO)CCO WXVGFWDXCCYEPR-RMKNXTFCSA-N 0.000 claims 1
- JFUAFGPNYRFZLM-RMKNXTFCSA-N [4-[2-[(e)-3-aminoprop-1-enyl]anilino]-2-chlorophenyl]-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1\C=C\CN JFUAFGPNYRFZLM-RMKNXTFCSA-N 0.000 claims 1
- AVJDYXLMKWKGBA-UHFFFAOYSA-N [4-[4-bromo-2-(2-hydroxyethoxymethyl)anilino]-2-chlorophenyl]-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=C(Br)C=C1COCCO AVJDYXLMKWKGBA-UHFFFAOYSA-N 0.000 claims 1
- JCZZHMWVHXQXHU-UHFFFAOYSA-N [4-[4-bromo-2-(2-hydroxyethyl)anilino]-2-chlorophenyl]-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=C(Br)C=C1CCO JCZZHMWVHXQXHU-UHFFFAOYSA-N 0.000 claims 1
- NULCISDQBUADCK-UHFFFAOYSA-N [4-[4-bromo-2-(2-iodoethoxymethyl)anilino]-2-chlorophenyl]-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=C(Br)C=C1COCCI NULCISDQBUADCK-UHFFFAOYSA-N 0.000 claims 1
- DXWSPIXAFVZGHT-UHFFFAOYSA-N [4-[4-bromo-2-(3,3,3-trifluoropropoxymethyl)anilino]-2-chlorophenyl]-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=C(Br)C=C1COCCC(F)(F)F DXWSPIXAFVZGHT-UHFFFAOYSA-N 0.000 claims 1
- XFTJYHJVCHZYBM-UHFFFAOYSA-N [4-[4-bromo-2-[2-(2-hydroxyethoxy)ethoxymethyl]anilino]-2-chlorophenyl]-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=C(Br)C=C1COCCOCCO XFTJYHJVCHZYBM-UHFFFAOYSA-N 0.000 claims 1
- OSGAAUHVJDRMFG-UHFFFAOYSA-N [4-[4-bromo-2-[2-(2-iodoethoxy)ethoxymethyl]anilino]-2-chlorophenyl]-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=C(Br)C=C1COCCOCCI OSGAAUHVJDRMFG-UHFFFAOYSA-N 0.000 claims 1
- PFTMLRHSNFPNOG-UHFFFAOYSA-N [4-[4-bromo-2-[2-[2-(2-hydroxyethoxy)ethoxy]ethoxymethyl]anilino]-2-chlorophenyl]-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=C(Br)C=C1COCCOCCOCCO PFTMLRHSNFPNOG-UHFFFAOYSA-N 0.000 claims 1
- IXCLKUJQTNNPQM-UHFFFAOYSA-N [4-[4-bromo-2-[2-[2-(2-iodoethoxy)ethoxy]ethoxymethyl]anilino]-2-chlorophenyl]-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=C(Br)C=C1COCCOCCOCCI IXCLKUJQTNNPQM-UHFFFAOYSA-N 0.000 claims 1
- 239000000464 adrenergic agent Substances 0.000 claims 1
- 239000000808 adrenergic beta-agonist Substances 0.000 claims 1
- 229940065524 anticholinergics inhalants for obstructive airway diseases Drugs 0.000 claims 1
- 229940007550 benzyl acetate Drugs 0.000 claims 1
- OGBVRMYSNSKIEF-UHFFFAOYSA-L benzyl-dioxido-oxo-$l^{5}-phosphane Chemical compound [O-]P([O-])(=O)CC1=CC=CC=C1 OGBVRMYSNSKIEF-UHFFFAOYSA-L 0.000 claims 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 1
- QUKGYYKBILRGFE-UHFFFAOYSA-N benzyloxyacetoaldehyde Natural products CC(=O)OCC1=CC=CC=C1 QUKGYYKBILRGFE-UHFFFAOYSA-N 0.000 claims 1
- SNCZNSNPXMPCGN-UHFFFAOYSA-N butanediamide Chemical compound NC(=O)CCC(N)=O SNCZNSNPXMPCGN-UHFFFAOYSA-N 0.000 claims 1
- SHZIWNPUGXLXDT-UHFFFAOYSA-N caproic acid ethyl ester Natural products CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 claims 1
- VDEJJAPWKNTANO-DHZHZOJOSA-N ethyl 4-[[(e)-3-[2-[3-chloro-4-(2-methylbenzoyl)anilino]phenyl]prop-2-enyl]amino]-4-oxobutanoate Chemical compound CCOC(=O)CCC(=O)NC\C=C\C1=CC=CC=C1NC(C=C1Cl)=CC=C1C(=O)C1=CC=CC=C1C VDEJJAPWKNTANO-DHZHZOJOSA-N 0.000 claims 1
- VRZVPALEJCLXPR-UHFFFAOYSA-N ethyl 4-methylbenzenesulfonate Chemical compound CCOS(=O)(=O)C1=CC=C(C)C=C1 VRZVPALEJCLXPR-UHFFFAOYSA-N 0.000 claims 1
- GATNOFPXSDHULC-UHFFFAOYSA-N ethylphosphonic acid Chemical compound CCP(O)(O)=O GATNOFPXSDHULC-UHFFFAOYSA-N 0.000 claims 1
- 229940067594 flufenamate Drugs 0.000 claims 1
- LPEPZBJOKDYZAD-UHFFFAOYSA-N flufenamic acid Chemical compound OC(=O)C1=CC=CC=C1NC1=CC=CC(C(F)(F)F)=C1 LPEPZBJOKDYZAD-UHFFFAOYSA-N 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- ATGDOXJDPFRJPI-UHFFFAOYSA-N n'-[2-[3-chloro-4-(2-methylbenzoyl)anilino]phenyl]-n-(2,3-dihydroxypropyl)butanediamide Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1NC(=O)CCC(=O)NCC(O)CO ATGDOXJDPFRJPI-UHFFFAOYSA-N 0.000 claims 1
- ZOLPEBVPKJNOMH-UHFFFAOYSA-N n'-[2-[3-chloro-4-(2-methylbenzoyl)anilino]phenyl]-n-(4-phenoxybutyl)butanediamide Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1NC(=O)CCC(=O)NCCCCOC1=CC=CC=C1 ZOLPEBVPKJNOMH-UHFFFAOYSA-N 0.000 claims 1
- ITXSLCZPKOJHKM-UHFFFAOYSA-N n'-[2-[3-chloro-4-(2-methylbenzoyl)anilino]phenyl]-n-(6-hydroxyhexyl)butanediamide Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1NC(=O)CCC(=O)NCCCCCCO ITXSLCZPKOJHKM-UHFFFAOYSA-N 0.000 claims 1
- XGXYMJHEYXZLMP-UHFFFAOYSA-N n'-[5-bromo-2-[3-chloro-4-(2-methylbenzoyl)anilino]phenyl]-n-(6-hydroxyhexyl)butanediamide Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=C(Br)C=C1NC(=O)CCC(=O)NCCCCCCO XGXYMJHEYXZLMP-UHFFFAOYSA-N 0.000 claims 1
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 claims 1
- ZAKPKHQMZLLVTC-JXMROGBWSA-N n-[(e)-3-[2-[3-chloro-4-(2-methylbenzoyl)anilino]phenyl]prop-2-enyl]-4-oxopentanamide Chemical compound CC(=O)CCC(=O)NC\C=C\C1=CC=CC=C1NC(C=C1Cl)=CC=C1C(=O)C1=CC=CC=C1C ZAKPKHQMZLLVTC-JXMROGBWSA-N 0.000 claims 1
- MJVQXHCLJPERKH-DHZHZOJOSA-N n-[(e)-3-[2-[3-chloro-4-(2-methylbenzoyl)anilino]phenyl]prop-2-enyl]-n',n'-dimethylbutanediamide Chemical compound CN(C)C(=O)CCC(=O)NC\C=C\C1=CC=CC=C1NC(C=C1Cl)=CC=C1C(=O)C1=CC=CC=C1C MJVQXHCLJPERKH-DHZHZOJOSA-N 0.000 claims 1
- PNBZPYJGHSNMLZ-UHFFFAOYSA-N n-[2-[3-chloro-4-(2-methylbenzoyl)anilino]phenyl]-2-(1,3-dioxoisoindol-2-yl)acetamide Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1NC(=O)CN1C(=O)C2=CC=CC=C2C1=O PNBZPYJGHSNMLZ-UHFFFAOYSA-N 0.000 claims 1
- KQIVIHYEWZURJE-UHFFFAOYSA-N n-[2-[3-chloro-4-(2-methylbenzoyl)anilino]phenyl]-2-phenoxyacetamide Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1NC(=O)COC1=CC=CC=C1 KQIVIHYEWZURJE-UHFFFAOYSA-N 0.000 claims 1
- VPWXAHSRVLNJSH-UHFFFAOYSA-N n-[2-[3-chloro-4-(2-methylbenzoyl)anilino]phenyl]-3-phenoxypropanamide Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1NC(=O)CCOC1=CC=CC=C1 VPWXAHSRVLNJSH-UHFFFAOYSA-N 0.000 claims 1
- PJJFHEJUYZFWNP-UHFFFAOYSA-N n-[2-[3-chloro-4-(2-methylbenzoyl)anilino]phenyl]benzenesulfonamide Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1NS(=O)(=O)C1=CC=CC=C1 PJJFHEJUYZFWNP-UHFFFAOYSA-N 0.000 claims 1
- DXWVFCUYNUGRRS-UHFFFAOYSA-N n-[5-bromo-2-[3-chloro-4-(2-methylbenzoyl)anilino]phenyl]-2,2,2-trifluoroethanesulfonamide Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=C(Br)C=C1NS(=O)(=O)CC(F)(F)F DXWVFCUYNUGRRS-UHFFFAOYSA-N 0.000 claims 1
- LZEVFMLEWXZBFJ-UHFFFAOYSA-N n-[5-bromo-2-[3-chloro-4-(2-methylbenzoyl)anilino]phenyl]-2-diethoxyphosphorylacetamide Chemical compound CCOP(=O)(OCC)CC(=O)NC1=CC(Br)=CC=C1NC(C=C1Cl)=CC=C1C(=O)C1=CC=CC=C1C LZEVFMLEWXZBFJ-UHFFFAOYSA-N 0.000 claims 1
- VBWGTFYHSBSYNK-UHFFFAOYSA-N n-[[2-[3-chloro-4-(2-methylbenzoyl)anilino]phenyl]methyl]-2,2,2-trifluoroethanesulfonamide Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1CNS(=O)(=O)CC(F)(F)F VBWGTFYHSBSYNK-UHFFFAOYSA-N 0.000 claims 1
- UEELGLGKUMDWQK-UHFFFAOYSA-N n-[[2-[3-chloro-4-(2-methylbenzoyl)anilino]phenyl]methyl]-2-diethoxyphosphorylacetamide Chemical compound CCOP(=O)(OCC)CC(=O)NCC1=CC=CC=C1NC(C=C1Cl)=CC=C1C(=O)C1=CC=CC=C1C UEELGLGKUMDWQK-UHFFFAOYSA-N 0.000 claims 1
- 229960001639 penicillamine Drugs 0.000 claims 1
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 claims 1
- FKRCODPIKNYEAC-UHFFFAOYSA-N propionic acid ethyl ester Natural products CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 claims 1
- 229940090181 propyl acetate Drugs 0.000 claims 1
- 150000004492 retinoid derivatives Chemical class 0.000 claims 1
- SDKPSXWGRWWLKR-UHFFFAOYSA-M sodium;9,10-dioxoanthracene-1-sulfonate Chemical compound [Na+].O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2S(=O)(=O)[O-] SDKPSXWGRWWLKR-UHFFFAOYSA-M 0.000 claims 1
- NCEXYHBECQHGNR-QZQOTICOSA-N sulfasalazine Chemical compound C1=C(O)C(C(=O)O)=CC(\N=N\C=2C=CC(=CC=2)S(=O)(=O)NC=2N=CC=CC=2)=C1 NCEXYHBECQHGNR-QZQOTICOSA-N 0.000 claims 1
- 229960001940 sulfasalazine Drugs 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 239000011593 sulfur Substances 0.000 claims 1
- KKTRUMAPENRITH-UHFFFAOYSA-N tert-butyl 2-[2-[3-chloro-4-(2-methylbenzoyl)anilino]phenyl]ethyl carbonate Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1CCOC(=O)OC(C)(C)C KKTRUMAPENRITH-UHFFFAOYSA-N 0.000 claims 1
- 150000003751 zinc Chemical class 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US31502501P | 2001-08-28 | 2001-08-28 | |
| DKPA200200189 | 2002-02-08 | ||
| PCT/DK2002/000557 WO2003018535A2 (en) | 2001-08-28 | 2002-08-26 | Novel aminobenzoephenones |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010089290A Division JP2010189410A (ja) | 2001-08-28 | 2010-04-08 | 新規アミノベンゾフェノン |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2005500400A JP2005500400A (ja) | 2005-01-06 |
| JP2005500400A5 true JP2005500400A5 (https=) | 2006-01-05 |
| JP4540984B2 JP4540984B2 (ja) | 2010-09-08 |
Family
ID=26069134
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003523200A Expired - Fee Related JP4540984B2 (ja) | 2001-08-28 | 2002-08-26 | 新規アミノベンゾフェノン |
| JP2010089290A Pending JP2010189410A (ja) | 2001-08-28 | 2010-04-08 | 新規アミノベンゾフェノン |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010089290A Pending JP2010189410A (ja) | 2001-08-28 | 2010-04-08 | 新規アミノベンゾフェノン |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US7034015B2 (https=) |
| EP (1) | EP1423356A2 (https=) |
| JP (2) | JP4540984B2 (https=) |
| KR (1) | KR100896667B1 (https=) |
| CN (1) | CN100347151C (https=) |
| AU (1) | AU2002331310B2 (https=) |
| BR (1) | BR0212249A (https=) |
| CA (1) | CA2458611C (https=) |
| HU (1) | HUP0401644A3 (https=) |
| IL (2) | IL160442A0 (https=) |
| MX (1) | MXPA04001912A (https=) |
| PL (1) | PL207487B1 (https=) |
| RU (1) | RU2361855C2 (https=) |
| WO (1) | WO2003018535A2 (https=) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7129229B2 (en) * | 2000-08-11 | 2006-10-31 | Nanogen Recognomics Gmbh | Hydrazide building blocks and hydrazide modified biomolecules |
| KR100896667B1 (ko) * | 2001-08-28 | 2009-05-14 | 레오 파마 에이/에스 | 신규한 아미노벤조페논 및 이를 포함하는 약제학적 조성물 |
| PL377377A1 (pl) * | 2002-12-20 | 2006-02-06 | Leo Pharma A/S | Nowe związki aminobenzofenonu |
| DK1658263T3 (da) * | 2003-07-24 | 2010-09-27 | Leo Pharma As | Aminobenzophenonforbindelser |
| KR101260236B1 (ko) | 2004-12-13 | 2013-05-06 | 레오 파마 에이/에스 | 트리아졸 치환된 아미노벤조페논 화합물 |
| DE102005022020A1 (de) * | 2005-05-12 | 2006-11-23 | Merckle Gmbh | Dibenzocycloheptanverbindungen und pharmazeutische Mittel, welche diese Verbindungen enthalten |
| EP2206534A1 (de) | 2008-10-09 | 2010-07-14 | c-a-i-r biosciences GmbH | Dibenzocycloheptanonderivate und pharmazeutische Mittel, welche diese Verbindungen enthalten |
| AU2010301449B2 (en) * | 2009-09-30 | 2013-03-14 | Toray Industries, Inc. | 2,3-dihydro-1H-indene-2-ylurea derivative and pharmaceutical application of same |
| KR102098606B1 (ko) * | 2012-10-31 | 2020-04-09 | 후지필름 도야마 케미컬 가부시키가이샤 | 신규 아민 유도체 또는 그 염 |
| US9758445B2 (en) * | 2013-04-09 | 2017-09-12 | Materia, Inc. | Preparation of surfactants via cross-metathesis |
| WO2015126462A1 (en) * | 2014-02-19 | 2015-08-27 | Materia, Inc. | Preparation of surfactants via cross-metathesis |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57177058A (en) | 1981-04-24 | 1982-10-30 | Hodogaya Chem Co Ltd | Novel fluoran compound |
| EP0859771A4 (en) * | 1995-10-31 | 2000-03-15 | Merck & Co Inc | SUBSTITUTED PYRIDYLPYRROLE, PREPARATIONS CONTAINING SUCH COMPOUNDS AND METHOD FOR THE USE THEREOF |
| GB9701453D0 (en) * | 1997-01-24 | 1997-03-12 | Leo Pharm Prod Ltd | Aminobenzophenones |
| JPH11349568A (ja) * | 1998-06-08 | 1999-12-21 | Maruho Co Ltd | ラクタム誘導体及びその医薬用途 |
| RU2240995C2 (ru) * | 1999-07-16 | 2004-11-27 | Лео Фармасьютикал Продактс Лтд.А/С (Левенс Кемиске Фабрик Продукционсактиесельскаб) | Аминобензофеноны в качестве ингибиторов интерлейкина il-1бета и фактора некроза опухолей tnf-альфа |
| EP1210325B1 (en) * | 1999-07-16 | 2004-10-06 | Leo Pharma A/S | Aminobenzophenones as inhibitors of il-1beta and tnf-alpha |
| ES2228555T3 (es) * | 1999-07-16 | 2005-04-16 | Leo Pharma A/S | Aminobenzofenonas con inhibidores de la il-1beta y tnf-alfa. |
| AU768473B2 (en) | 1999-07-16 | 2003-12-11 | Leo Pharmaceutical Products Ltd. A/S (Lovens Kemiske Fabrik Produktionsaktieselskab) | Novel aminobenzophenones |
| ATE277889T1 (de) | 1999-07-16 | 2004-10-15 | Leo Pharma As | Aminobenzophenone als inhibitoren von il-1beta und tnf-alpha |
| MXPA02005604A (es) * | 1999-12-06 | 2004-09-10 | Leo Pharma As | Aminobenzofenonas como inhibidores de il-1beta y tnf-alfa. |
| AU2001260081B2 (en) * | 2000-05-22 | 2005-07-28 | Leo Pharma A/S | Benzophenones as inhibitors of il-1beta and tnf-alpha |
| US20020165286A1 (en) * | 2000-12-08 | 2002-11-07 | Hanne Hedeman | Dermal anti-inflammatory composition |
| KR100896667B1 (ko) * | 2001-08-28 | 2009-05-14 | 레오 파마 에이/에스 | 신규한 아미노벤조페논 및 이를 포함하는 약제학적 조성물 |
-
2002
- 2002-08-26 KR KR1020047003014A patent/KR100896667B1/ko not_active Expired - Fee Related
- 2002-08-26 JP JP2003523200A patent/JP4540984B2/ja not_active Expired - Fee Related
- 2002-08-26 IL IL16044202A patent/IL160442A0/xx unknown
- 2002-08-26 PL PL368686A patent/PL207487B1/pl not_active IP Right Cessation
- 2002-08-26 CN CNB028193571A patent/CN100347151C/zh not_active Expired - Fee Related
- 2002-08-26 MX MXPA04001912A patent/MXPA04001912A/es active IP Right Grant
- 2002-08-26 AU AU2002331310A patent/AU2002331310B2/en not_active Ceased
- 2002-08-26 EP EP02767145A patent/EP1423356A2/en not_active Withdrawn
- 2002-08-26 WO PCT/DK2002/000557 patent/WO2003018535A2/en not_active Ceased
- 2002-08-26 HU HU0401644A patent/HUP0401644A3/hu unknown
- 2002-08-26 RU RU2004109142/04A patent/RU2361855C2/ru not_active IP Right Cessation
- 2002-08-26 BR BR0212249-9A patent/BR0212249A/pt active Search and Examination
- 2002-08-26 CA CA2458611A patent/CA2458611C/en not_active Expired - Fee Related
- 2002-08-28 US US10/228,954 patent/US7034015B2/en not_active Expired - Fee Related
-
2004
- 2004-02-17 IL IL160442A patent/IL160442A/en not_active IP Right Cessation
-
2010
- 2010-04-08 JP JP2010089290A patent/JP2010189410A/ja active Pending
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| RU2008112683A (ru) | Ингибиторы fap | |
| JP2005500400A5 (https=) | ||
| US20260102382A1 (en) | Methods for treatment of fibrotic diseases | |
| JP2005536475A5 (https=) | ||
| RU2004104625A (ru) | Аналоги простагландинов в качестве агонистов рецептора ep4 | |
| RU99105119A (ru) | Производные пурина и их применение в качестве антикоагулянтов | |
| AU2010200833B2 (en) | Use of renin inhibitors for the prevention or treatment of diastolic dysfunction or diastolic heart failure | |
| CN101102757A (zh) | 治疗多囊性肾疾病的方法 | |
| RU2006105639A (ru) | Новые производные аминобензофенона | |
| EP3681861A1 (en) | Cxcr-2 inhibitors for treating disorders | |
| US20090247582A1 (en) | Methods of treating atherosclerosis | |
| RU2004109142A (ru) | Новые аминобензофеноны | |
| RU2331438C2 (ru) | Альфа-2-дельта лиганд для лечения симптомов нижних мочевыводящих путей | |
| TW201912153A (zh) | 用於治療ｂ型肝炎的化合物、醫藥組合物及方法 | |
| US20080261958A1 (en) | Combination of Organic Compounds | |
| JP2021522270A5 (https=) | ||
| AU2019274870B2 (en) | Method of treating pain or interstitial cystitis using indole compound | |
| WO2002045750A1 (en) | Combination drugs | |
| TW200306853A (en) | Therapeutic agent for glomerular disease | |
| RU2006131043A (ru) | Соединения силинана в качестве ингибиторов цистеиновой протеазы | |
| JP2007509052A5 (https=) | ||
| RU2017141405A (ru) | Соединения, обладающие активностью антагонистов мускариновых рецепторов и агонистов бета-2-адренергических рецепторов | |
| RU2003104804A (ru) | Ингибиторы матриксной металлопротеиназы | |
| EP1642594A1 (en) | Remedy for urinary tract diseases | |
| RU2007115092A (ru) | Аминоспиртовые производные |