RU2396250C2 - Новые производные аминобензофенона - Google Patents
Новые производные аминобензофенона Download PDFInfo
- Publication number
- RU2396250C2 RU2396250C2 RU2006105639/04A RU2006105639A RU2396250C2 RU 2396250 C2 RU2396250 C2 RU 2396250C2 RU 2006105639/04 A RU2006105639/04 A RU 2006105639/04A RU 2006105639 A RU2006105639 A RU 2006105639A RU 2396250 C2 RU2396250 C2 RU 2396250C2
- Authority
- RU
- Russia
- Prior art keywords
- compound
- chloro
- benzoyl
- difluorophenylamino
- methylbenzamide
- Prior art date
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- MAOBFOXLCJIFLV-UHFFFAOYSA-N (2-aminophenyl)-phenylmethanone Chemical class NC1=CC=CC=C1C(=O)C1=CC=CC=C1 MAOBFOXLCJIFLV-UHFFFAOYSA-N 0.000 title description 9
- 150000001875 compounds Chemical class 0.000 claims abstract description 1576
- -1 C1-4alkylthio Chemical group 0.000 claims abstract description 174
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 44
- 239000001257 hydrogen Substances 0.000 claims abstract description 44
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 34
- 150000002367 halogens Chemical group 0.000 claims abstract description 34
- 125000001424 substituent group Chemical group 0.000 claims abstract description 31
- 150000002431 hydrogen Chemical group 0.000 claims abstract description 29
- 108060008682 Tumor Necrosis Factor Proteins 0.000 claims abstract description 21
- 102000000852 Tumor Necrosis Factor-alpha Human genes 0.000 claims abstract description 21
- MZOFCQQQCNRIBI-VMXHOPILSA-N (3s)-4-[[(2s)-1-[[(2s)-1-[[(1s)-1-carboxy-2-hydroxyethyl]amino]-4-methyl-1-oxopentan-2-yl]amino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-3-[[2-[[(2s)-2,6-diaminohexanoyl]amino]acetyl]amino]-4-oxobutanoic acid Chemical compound OC[C@@H](C(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CC(O)=O)NC(=O)CNC(=O)[C@@H](N)CCCCN MZOFCQQQCNRIBI-VMXHOPILSA-N 0.000 claims abstract description 19
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 19
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 14
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 12
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 11
- 239000003112 inhibitor Substances 0.000 claims abstract description 7
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims abstract description 6
- 239000003814 drug Substances 0.000 claims abstract description 5
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims abstract description 3
- 239000002246 antineoplastic agent Substances 0.000 claims abstract description 3
- 101710203984 Mitogen-activated protein kinase 14A Proteins 0.000 claims abstract 2
- 239000002260 anti-inflammatory agent Substances 0.000 claims abstract 2
- 229940079593 drug Drugs 0.000 claims abstract 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 446
- 238000006243 chemical reaction Methods 0.000 claims description 189
- 125000000217 alkyl group Chemical group 0.000 claims description 74
- 150000001412 amines Chemical class 0.000 claims description 59
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 55
- 238000000034 method Methods 0.000 claims description 40
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 37
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 31
- 125000003545 alkoxy group Chemical group 0.000 claims description 23
- 125000004452 carbocyclyl group Chemical group 0.000 claims description 22
- 239000000460 chlorine Substances 0.000 claims description 22
- 150000002148 esters Chemical class 0.000 claims description 21
- 125000000524 functional group Chemical group 0.000 claims description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 15
- 229920006395 saturated elastomer Polymers 0.000 claims description 15
- UHNRLQRZRNKOKU-UHFFFAOYSA-N CCN(CC1=NC2=C(N1)C1=CC=C(C=C1N=C2N)C1=NNC=C1)C(C)=O Chemical compound CCN(CC1=NC2=C(N1)C1=CC=C(C=C1N=C2N)C1=NNC=C1)C(C)=O UHNRLQRZRNKOKU-UHFFFAOYSA-N 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- 150000004820 halides Chemical class 0.000 claims description 12
- 125000004414 alkyl thio group Chemical group 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 10
- 125000001153 fluoro group Chemical group F* 0.000 claims description 10
- 125000002524 organometallic group Chemical group 0.000 claims description 10
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 9
- NVCGUCYXULPVAO-UHFFFAOYSA-N 3-[2-chloro-4-(2,4-difluoroanilino)benzoyl]-4-methylbenzoic acid Chemical compound CC1=CC=C(C(O)=O)C=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=C(F)C=C1F NVCGUCYXULPVAO-UHFFFAOYSA-N 0.000 claims description 8
- DEKOTVGACVBSJQ-UHFFFAOYSA-N 3-[2-chloro-4-(2,4-difluoroanilino)benzoyl]-4-methyl-n-propan-2-ylbenzamide Chemical compound CC(C)NC(=O)C1=CC=C(C)C(C(=O)C=2C(=CC(NC=3C(=CC(F)=CC=3)F)=CC=2)Cl)=C1 DEKOTVGACVBSJQ-UHFFFAOYSA-N 0.000 claims description 7
- UEBNDNCNOYGFHU-UHFFFAOYSA-N 3-[2-chloro-4-(2,4-difluoroanilino)benzoyl]-n-(1,3-dihydroxy-2-methylpropan-2-yl)-4-methylbenzamide Chemical compound CC1=CC=C(C(=O)NC(C)(CO)CO)C=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=C(F)C=C1F UEBNDNCNOYGFHU-UHFFFAOYSA-N 0.000 claims description 7
- AVGNIXREWPXTQQ-UHFFFAOYSA-N 3-[2-chloro-4-(2,4-difluoroanilino)benzoyl]-n-(1-hydroxy-2-methylpropan-2-yl)-4-methylbenzamide Chemical compound CC1=CC=C(C(=O)NC(C)(C)CO)C=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=C(F)C=C1F AVGNIXREWPXTQQ-UHFFFAOYSA-N 0.000 claims description 7
- XJKXXPPFYLOJPV-UHFFFAOYSA-N 3-[2-chloro-4-(2,4-difluoroanilino)benzoyl]-n-(2,2-difluoroethyl)-4-methoxybenzamide Chemical compound COC1=CC=C(C(=O)NCC(F)F)C=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=C(F)C=C1F XJKXXPPFYLOJPV-UHFFFAOYSA-N 0.000 claims description 7
- RODQBFPVTHIQGB-UHFFFAOYSA-N 3-[2-chloro-4-(2,4-difluoroanilino)benzoyl]-n-(2-fluoroethyl)-4-methylbenzamide Chemical compound CC1=CC=C(C(=O)NCCF)C=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=C(F)C=C1F RODQBFPVTHIQGB-UHFFFAOYSA-N 0.000 claims description 7
- OPMURCUOUWTRJV-UHFFFAOYSA-N 3-[2-chloro-4-(2,4-difluoroanilino)benzoyl]-n-(3-hydroxypropyl)-4-methylbenzamide Chemical compound CC1=CC=C(C(=O)NCCCO)C=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=C(F)C=C1F OPMURCUOUWTRJV-UHFFFAOYSA-N 0.000 claims description 7
- DGQMCGBWYSNJJI-UHFFFAOYSA-N 3-[2-chloro-4-(2,4-difluoroanilino)benzoyl]-n-ethyl-4-methylbenzamide Chemical compound CCNC(=O)C1=CC=C(C)C(C(=O)C=2C(=CC(NC=3C(=CC(F)=CC=3)F)=CC=2)Cl)=C1 DGQMCGBWYSNJJI-UHFFFAOYSA-N 0.000 claims description 7
- OLTZQIHCMBOBQJ-UHFFFAOYSA-N 3-[2-chloro-4-(2,6-difluoroanilino)benzoyl]-n-(1-hydroxy-2-methylpropan-2-yl)-4-methoxybenzamide Chemical compound COC1=CC=C(C(=O)NC(C)(C)CO)C=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=C(F)C=CC=C1F OLTZQIHCMBOBQJ-UHFFFAOYSA-N 0.000 claims description 7
- HTPPBPAWLFGFAA-UHFFFAOYSA-N 3-[2-chloro-4-(2,6-difluoroanilino)benzoyl]-n-(2-hydroxyethyl)-4-methoxybenzamide Chemical compound COC1=CC=C(C(=O)NCCO)C=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=C(F)C=CC=C1F HTPPBPAWLFGFAA-UHFFFAOYSA-N 0.000 claims description 7
- CPAWJQZRACNQGR-UHFFFAOYSA-N 3-[2-chloro-4-(2,6-difluoroanilino)benzoyl]-n-(3-hydroxypropyl)-4-methoxybenzamide Chemical compound COC1=CC=C(C(=O)NCCCO)C=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=C(F)C=CC=C1F CPAWJQZRACNQGR-UHFFFAOYSA-N 0.000 claims description 7
- MBKIZRXNUBAEAK-UHFFFAOYSA-N 3-[2-chloro-4-(2-chloro-4-fluoroanilino)benzoyl]-n-(2-hydroxyethyl)-4-methylbenzamide Chemical compound CC1=CC=C(C(=O)NCCO)C=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=C(F)C=C1Cl MBKIZRXNUBAEAK-UHFFFAOYSA-N 0.000 claims description 7
- WJQAPXGFTAZTMF-UHFFFAOYSA-N 3-[2-chloro-4-(3-fluoro-2-methylanilino)benzoyl]-n-(2-hydroxyethyl)-4-methylbenzamide Chemical compound CC1=CC=C(C(=O)NCCO)C=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC(F)=C1C WJQAPXGFTAZTMF-UHFFFAOYSA-N 0.000 claims description 7
- YDXKBKBLZDYNGS-UHFFFAOYSA-N 3-[2-chloro-4-(4-chloro-2-fluoroanilino)benzoyl]-n-(2-hydroxyethyl)-4-methylbenzamide Chemical compound CC1=CC=C(C(=O)NCCO)C=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=C(Cl)C=C1F YDXKBKBLZDYNGS-UHFFFAOYSA-N 0.000 claims description 7
- JDNRTMUBDGCKDB-UHFFFAOYSA-N 3-[4-(2-amino-4-bromoanilino)-2-chlorobenzoyl]-n-(2-hydroxyethyl)-4-methylbenzamide Chemical compound CC1=CC=C(C(=O)NCCO)C=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=C(Br)C=C1N JDNRTMUBDGCKDB-UHFFFAOYSA-N 0.000 claims description 7
- FSJLRPIFRXFXFY-UHFFFAOYSA-N 3-[4-(2-aminoanilino)-2-chlorobenzoyl]-n-ethyl-4-methylbenzamide Chemical compound CCNC(=O)C1=CC=C(C)C(C(=O)C=2C(=CC(NC=3C(=CC=CC=3)N)=CC=2)Cl)=C1 FSJLRPIFRXFXFY-UHFFFAOYSA-N 0.000 claims description 7
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 7
- JMCBKPGHVVWDPS-UHFFFAOYSA-N ethyl 2-[[3-[2-chloro-4-(4-chloro-2-fluoroanilino)benzoyl]-4-methylbenzoyl]amino]acetate Chemical compound CCOC(=O)CNC(=O)C1=CC=C(C)C(C(=O)C=2C(=CC(NC=3C(=CC(Cl)=CC=3)F)=CC=2)Cl)=C1 JMCBKPGHVVWDPS-UHFFFAOYSA-N 0.000 claims description 7
- 229910052731 fluorine Inorganic materials 0.000 claims description 7
- PCMWFRZEEUCKDV-UHFFFAOYSA-N n-(2-amino-2-oxoethyl)-3-[2-chloro-4-(2,4-difluoroanilino)benzoyl]-4-methylbenzamide Chemical compound CC1=CC=C(C(=O)NCC(N)=O)C=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=C(F)C=C1F PCMWFRZEEUCKDV-UHFFFAOYSA-N 0.000 claims description 7
- NARDOQOBDJHIDY-UHFFFAOYSA-N n-[3-[2-chloro-4-(2,4-difluoroanilino)benzoyl]-4-methylphenyl]-3-methylsulfanylpropanamide Chemical compound CSCCC(=O)NC1=CC=C(C)C(C(=O)C=2C(=CC(NC=3C(=CC(F)=CC=3)F)=CC=2)Cl)=C1 NARDOQOBDJHIDY-UHFFFAOYSA-N 0.000 claims description 7
- RGVFOADAKVPCMU-UHFFFAOYSA-N prop-2-enyl n-[3-[2-chloro-4-(2,4-difluoroanilino)benzoyl]-4-methylphenyl]carbamate Chemical compound CC1=CC=C(NC(=O)OCC=C)C=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=C(F)C=C1F RGVFOADAKVPCMU-UHFFFAOYSA-N 0.000 claims description 7
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims description 7
- NDODFKPCVYMIQS-UHFFFAOYSA-N 1-[3-[2-chloro-4-(2,4-difluoroanilino)benzoyl]-4-methylphenyl]-3-(2-hydroxyethyl)urea Chemical compound CC1=CC=C(NC(=O)NCCO)C=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=C(F)C=C1F NDODFKPCVYMIQS-UHFFFAOYSA-N 0.000 claims description 6
- DXGHYSHCFFXHIW-UHFFFAOYSA-N 1-[3-[2-chloro-4-(2,4-difluoroanilino)benzoyl]-4-methylphenyl]-3-cyclohexylurea Chemical compound C1=C(C(=O)C=2C(=CC(NC=3C(=CC(F)=CC=3)F)=CC=2)Cl)C(C)=CC=C1NC(=O)NC1CCCCC1 DXGHYSHCFFXHIW-UHFFFAOYSA-N 0.000 claims description 6
- AGVCFAYVWSTPDZ-UHFFFAOYSA-N 1-[3-[2-chloro-4-(2,4-difluoroanilino)benzoyl]-4-methylphenyl]-3-propan-2-ylurea Chemical compound CC(C)NC(=O)NC1=CC=C(C)C(C(=O)C=2C(=CC(NC=3C(=CC(F)=CC=3)F)=CC=2)Cl)=C1 AGVCFAYVWSTPDZ-UHFFFAOYSA-N 0.000 claims description 6
- BCPMNNFMKAZEGR-UHFFFAOYSA-N 1-butyl-3-[3-[2-chloro-4-(2,4-difluoroanilino)benzoyl]-4-methylphenyl]urea Chemical compound CCCCNC(=O)NC1=CC=C(C)C(C(=O)C=2C(=CC(NC=3C(=CC(F)=CC=3)F)=CC=2)Cl)=C1 BCPMNNFMKAZEGR-UHFFFAOYSA-N 0.000 claims description 6
- XQHSCIHGMAUTLU-UHFFFAOYSA-N 3-(4-anilino-2-chlorobenzoyl)-n-(2,3-dihydroxypropyl)-4-methoxybenzamide Chemical compound COC1=CC=C(C(=O)NCC(O)CO)C=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1 XQHSCIHGMAUTLU-UHFFFAOYSA-N 0.000 claims description 6
- KOPSDWMYDJDINE-UHFFFAOYSA-N 3-[2-chloro-4-(2,4-difluoroanilino)benzoyl]-n-(1-hydroxybutan-2-yl)-4-methylbenzamide Chemical compound CCC(CO)NC(=O)C1=CC=C(C)C(C(=O)C=2C(=CC(NC=3C(=CC(F)=CC=3)F)=CC=2)Cl)=C1 KOPSDWMYDJDINE-UHFFFAOYSA-N 0.000 claims description 6
- CPGVKHMDMAMUJI-UHFFFAOYSA-N 3-[2-chloro-4-(2,4-difluoroanilino)benzoyl]-n-(2,2-difluoroethyl)-4-methylbenzamide Chemical compound CC1=CC=C(C(=O)NCC(F)F)C=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=C(F)C=C1F CPGVKHMDMAMUJI-UHFFFAOYSA-N 0.000 claims description 6
- VDJDYDHUHCSRIY-UHFFFAOYSA-N 3-[2-chloro-4-(2,4-difluoroanilino)benzoyl]-n-(2,3-dihydroxypropyl)-4-methylbenzamide Chemical compound CC1=CC=C(C(=O)NCC(O)CO)C=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=C(F)C=C1F VDJDYDHUHCSRIY-UHFFFAOYSA-N 0.000 claims description 6
- XAGXOVYPPZPYSV-UHFFFAOYSA-N 3-[2-chloro-4-(2,4-difluoroanilino)benzoyl]-n-(2-hydroxyethyl)-4-methoxybenzamide Chemical compound COC1=CC=C(C(=O)NCCO)C=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=C(F)C=C1F XAGXOVYPPZPYSV-UHFFFAOYSA-N 0.000 claims description 6
- BLVKJKYLQMOUON-UHFFFAOYSA-N 3-[2-chloro-4-(2,4-difluoroanilino)benzoyl]-n-(4-hydroxybutyl)-4-methylbenzamide Chemical compound CC1=CC=C(C(=O)NCCCCO)C=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=C(F)C=C1F BLVKJKYLQMOUON-UHFFFAOYSA-N 0.000 claims description 6
- SBTIWZSOKRDDRA-UHFFFAOYSA-N 3-[2-chloro-4-(4-chloro-2-fluoroanilino)benzoyl]-n,4-dimethylbenzamide Chemical compound CNC(=O)C1=CC=C(C)C(C(=O)C=2C(=CC(NC=3C(=CC(Cl)=CC=3)F)=CC=2)Cl)=C1 SBTIWZSOKRDDRA-UHFFFAOYSA-N 0.000 claims description 6
- CFJWRNVHKYLWAX-UHFFFAOYSA-N 3-[2-chloro-4-(4-chloro-2-fluoroanilino)benzoyl]-n-ethyl-4-methylbenzamide Chemical compound CCNC(=O)C1=CC=C(C)C(C(=O)C=2C(=CC(NC=3C(=CC(Cl)=CC=3)F)=CC=2)Cl)=C1 CFJWRNVHKYLWAX-UHFFFAOYSA-N 0.000 claims description 6
- XCKSSFFKYWEBNU-UHFFFAOYSA-N 3-[2-chloro-4-(4-fluoro-2-methylanilino)benzoyl]-n-(2-methoxyethyl)-4-methylbenzamide Chemical compound COCCNC(=O)C1=CC=C(C)C(C(=O)C=2C(=CC(NC=3C(=CC(F)=CC=3)C)=CC=2)Cl)=C1 XCKSSFFKYWEBNU-UHFFFAOYSA-N 0.000 claims description 6
- CFZFCOGVHCVEJE-UHFFFAOYSA-N 3-[2-chloro-4-(4-fluoroanilino)benzoyl]-n-(2,2-difluoroethyl)-4-methoxybenzamide Chemical compound COC1=CC=C(C(=O)NCC(F)F)C=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=C(F)C=C1 CFZFCOGVHCVEJE-UHFFFAOYSA-N 0.000 claims description 6
- GIMZGJKFCDGMLN-UHFFFAOYSA-N 3-[2-chloro-4-(4-fluoroanilino)benzoyl]-n-(2,3-dihydroxypropyl)-4-methoxybenzamide Chemical compound COC1=CC=C(C(=O)NCC(O)CO)C=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=C(F)C=C1 GIMZGJKFCDGMLN-UHFFFAOYSA-N 0.000 claims description 6
- JOFZGFOPROMAIT-UHFFFAOYSA-N 3-[4-(2,4-difluoroanilino)benzoyl]-n-(2-fluoroethyl)-4-methylbenzamide Chemical compound CC1=CC=C(C(=O)NCCF)C=C1C(=O)C(C=C1)=CC=C1NC1=CC=C(F)C=C1F JOFZGFOPROMAIT-UHFFFAOYSA-N 0.000 claims description 6
- VLUHTBBNOGVQLI-UHFFFAOYSA-N 3-[4-(4-bromo-2-methylanilino)-2-chlorobenzoyl]-n-(2-hydroxyethyl)-4-methylbenzamide Chemical compound CC1=CC(Br)=CC=C1NC(C=C1Cl)=CC=C1C(=O)C1=CC(C(=O)NCCO)=CC=C1C VLUHTBBNOGVQLI-UHFFFAOYSA-N 0.000 claims description 6
- GSDQYSSLIKJJOG-UHFFFAOYSA-N 4-chloro-2-(3-chloroanilino)benzoic acid Chemical compound OC(=O)C1=CC=C(Cl)C=C1NC1=CC=CC(Cl)=C1 GSDQYSSLIKJJOG-UHFFFAOYSA-N 0.000 claims description 6
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 6
- OGFASUGUCYIQIX-UHFFFAOYSA-N [2-chloro-4-(2,4-difluoroanilino)phenyl]-[5-[3-(hydroxymethyl)phenyl]-2-methylphenyl]methanone Chemical compound CC1=CC=C(C=2C=C(CO)C=CC=2)C=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=C(F)C=C1F OGFASUGUCYIQIX-UHFFFAOYSA-N 0.000 claims description 6
- OFXXQIJUOUGSJZ-UHFFFAOYSA-N benzyl n-[3-[2-chloro-4-(2,4-difluoroanilino)benzoyl]-4-methylphenyl]carbamate Chemical compound C1=C(C(=O)C=2C(=CC(NC=3C(=CC(F)=CC=3)F)=CC=2)Cl)C(C)=CC=C1NC(=O)OCC1=CC=CC=C1 OFXXQIJUOUGSJZ-UHFFFAOYSA-N 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- 125000001246 bromo group Chemical group Br* 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 6
- 239000011737 fluorine Substances 0.000 claims description 6
- GUGTYWYRLKEYQD-UHFFFAOYSA-N methyl 5-[[3-[2-chloro-4-(2,4-difluoroanilino)benzoyl]-4-methylbenzoyl]amino]-4-oxopentanoate Chemical compound COC(=O)CCC(=O)CNC(=O)C1=CC=C(C)C(C(=O)C=2C(=CC(NC=3C(=CC(F)=CC=3)F)=CC=2)Cl)=C1 GUGTYWYRLKEYQD-UHFFFAOYSA-N 0.000 claims description 6
- DZHXGQRSQQZDEH-UHFFFAOYSA-N n-(2-amino-2-oxoethyl)-3-[2-chloro-4-(2,4-difluoroanilino)benzoyl]-4-methoxybenzamide Chemical compound COC1=CC=C(C(=O)NCC(N)=O)C=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=C(F)C=C1F DZHXGQRSQQZDEH-UHFFFAOYSA-N 0.000 claims description 6
- LMNLGHKJGNIHAF-UHFFFAOYSA-N n-[2-[(3-amino-3-oxopropyl)amino]-2-oxoethyl]-3-[2-chloro-4-(2,4-difluoroanilino)benzoyl]-4-methylbenzamide Chemical compound CC1=CC=C(C(=O)NCC(=O)NCCC(N)=O)C=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=C(F)C=C1F LMNLGHKJGNIHAF-UHFFFAOYSA-N 0.000 claims description 6
- DDNSGLLJVPEMQV-UHFFFAOYSA-N n-[3-[3-[2-chloro-4-(2,4-difluoroanilino)benzoyl]-4-methylphenyl]phenyl]acetamide Chemical compound CC(=O)NC1=CC=CC(C=2C=C(C(C)=CC=2)C(=O)C=2C(=CC(NC=3C(=CC(F)=CC=3)F)=CC=2)Cl)=C1 DDNSGLLJVPEMQV-UHFFFAOYSA-N 0.000 claims description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims description 6
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
- 125000001544 thienyl group Chemical group 0.000 claims description 6
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- QYBAFRPZDKRKQM-UHFFFAOYSA-N 1-[3-[2-chloro-4-(2,4-difluoroanilino)benzoyl]-4-methylphenyl]-3-(4-methoxyphenyl)urea Chemical compound C1=CC(OC)=CC=C1NC(=O)NC1=CC=C(C)C(C(=O)C=2C(=CC(NC=3C(=CC(F)=CC=3)F)=CC=2)Cl)=C1 QYBAFRPZDKRKQM-UHFFFAOYSA-N 0.000 claims description 5
- VRTUCINXMHDFLP-UHFFFAOYSA-N 1-[3-[2-chloro-4-(2,4-difluoroanilino)benzoyl]-4-methylphenyl]-3-prop-2-enylurea Chemical compound CC1=CC=C(NC(=O)NCC=C)C=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=C(F)C=C1F VRTUCINXMHDFLP-UHFFFAOYSA-N 0.000 claims description 5
- LGVFXUNLSVJXFZ-UHFFFAOYSA-N 3-(4-anilino-2-chlorobenzoyl)-n-(2-fluoroethyl)-4-methoxybenzamide Chemical compound COC1=CC=C(C(=O)NCCF)C=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1 LGVFXUNLSVJXFZ-UHFFFAOYSA-N 0.000 claims description 5
- SVJMMEYQZJMPHQ-UHFFFAOYSA-N 3-(4-anilino-2-chlorobenzoyl)-n-(2-hydroxyethyl)-4-methoxybenzamide Chemical compound COC1=CC=C(C(=O)NCCO)C=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1 SVJMMEYQZJMPHQ-UHFFFAOYSA-N 0.000 claims description 5
- SLIYBLJAJWIESI-UHFFFAOYSA-N 3-(4-anilino-2-chlorobenzoyl)-n-(2-hydroxyethyl)-4-methylbenzamide Chemical compound CC1=CC=C(C(=O)NCCO)C=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1 SLIYBLJAJWIESI-UHFFFAOYSA-N 0.000 claims description 5
- ZFOFDSISXFUFSU-UHFFFAOYSA-N 3-[2-chloro-4-(2,4-difluoroanilino)benzoyl]-n-(2-fluoroethyl)-4-methoxybenzamide Chemical compound COC1=CC=C(C(=O)NCCF)C=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=C(F)C=C1F ZFOFDSISXFUFSU-UHFFFAOYSA-N 0.000 claims description 5
- OEEGZVCBHLXTAD-UHFFFAOYSA-N 3-[2-chloro-4-(2,4-difluoroanilino)benzoyl]-n-(4-hydroxy-2-methylpentan-2-yl)-4-methylbenzamide Chemical compound CC(O)CC(C)(C)NC(=O)C1=CC=C(C)C(C(=O)C=2C(=CC(NC=3C(=CC(F)=CC=3)F)=CC=2)Cl)=C1 OEEGZVCBHLXTAD-UHFFFAOYSA-N 0.000 claims description 5
- FDVXUBQUDFVTQT-HXUWFJFHSA-N 3-[2-chloro-4-(2,4-difluoroanilino)benzoyl]-n-[(2r)-1-hydroxy-4-methylpentan-2-yl]-4-methylbenzamide Chemical compound CC(C)C[C@H](CO)NC(=O)C1=CC=C(C)C(C(=O)C=2C(=CC(NC=3C(=CC(F)=CC=3)F)=CC=2)Cl)=C1 FDVXUBQUDFVTQT-HXUWFJFHSA-N 0.000 claims description 5
- KJXOSMASDGCSIK-UHFFFAOYSA-N 3-[2-chloro-4-(2,6-difluoroanilino)benzoyl]-n-(1,3-dihydroxy-2-methylpropan-2-yl)-4-methoxybenzamide Chemical compound COC1=CC=C(C(=O)NC(C)(CO)CO)C=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=C(F)C=CC=C1F KJXOSMASDGCSIK-UHFFFAOYSA-N 0.000 claims description 5
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- AHYJRBWUTHSYCQ-UHFFFAOYSA-N 3-[2-chloro-4-(2,6-difluoroanilino)benzoyl]-n-(2-hydroxyethyl)-4-methoxy-n-methylbenzamide Chemical compound COC1=CC=C(C(=O)N(C)CCO)C=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=C(F)C=CC=C1F AHYJRBWUTHSYCQ-UHFFFAOYSA-N 0.000 claims description 5
- PVSKHAGFNNXTOT-UHFFFAOYSA-N 3-[2-chloro-4-(3-fluoroanilino)benzoyl]-n-(2-hydroxyethyl)-4-methylbenzamide Chemical compound CC1=CC=C(C(=O)NCCO)C=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC(F)=C1 PVSKHAGFNNXTOT-UHFFFAOYSA-N 0.000 claims description 5
- SNSLHXGZRWRBSV-UHFFFAOYSA-N 3-[2-chloro-4-(4-fluoroanilino)benzoyl]-n-(2-hydroxyethyl)-4-methoxybenzamide Chemical compound COC1=CC=C(C(=O)NCCO)C=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=C(F)C=C1 SNSLHXGZRWRBSV-UHFFFAOYSA-N 0.000 claims description 5
- HMHHZAJHQMGPAN-UHFFFAOYSA-N 3-[2-chloro-4-(4-fluoroanilino)benzoyl]-n-(2-hydroxyethyl)-4-methylbenzamide Chemical compound CC1=CC=C(C(=O)NCCO)C=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=C(F)C=C1 HMHHZAJHQMGPAN-UHFFFAOYSA-N 0.000 claims description 5
- IRBAWVGZNJIROV-SFHVURJKSA-N 9-(2-cyclopropylethynyl)-2-[[(2s)-1,4-dioxan-2-yl]methoxy]-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C1=C2C3=CC=C(C#CC4CC4)C=C3CCN2C(=O)N=C1OC[C@@H]1COCCO1 IRBAWVGZNJIROV-SFHVURJKSA-N 0.000 claims description 5
- IYHHRZBKXXKDDY-UHFFFAOYSA-N BI-605906 Chemical compound N=1C=2SC(C(N)=O)=C(N)C=2C(C(F)(F)CC)=CC=1N1CCC(S(C)(=O)=O)CC1 IYHHRZBKXXKDDY-UHFFFAOYSA-N 0.000 claims description 5
- BGGALFIXXQOTPY-NRFANRHFSA-N C1(=C(C2=C(C=C1)N(C(C#N)=C2)C[C@@H](N1CCN(CC1)S(=O)(=O)C)C)C)CN1CCC(CC1)NC1=NC(=NC2=C1C=C(S2)CC(F)(F)F)NC Chemical compound C1(=C(C2=C(C=C1)N(C(C#N)=C2)C[C@@H](N1CCN(CC1)S(=O)(=O)C)C)C)CN1CCC(CC1)NC1=NC(=NC2=C1C=C(S2)CC(F)(F)F)NC BGGALFIXXQOTPY-NRFANRHFSA-N 0.000 claims description 5
- SCJNYBYSTCRPAO-LXBQGUBHSA-N CN(C)C\C=C\C(=O)NC1=CC=C(N=C1)C(=O)N[C@@]1(C)CCC[C@H](C1)NC1=NC(C2=CNC3=CC=CC=C23)=C(Cl)C=N1 Chemical compound CN(C)C\C=C\C(=O)NC1=CC=C(N=C1)C(=O)N[C@@]1(C)CCC[C@H](C1)NC1=NC(C2=CNC3=CC=CC=C23)=C(Cl)C=N1 SCJNYBYSTCRPAO-LXBQGUBHSA-N 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- POFVJRKJJBFPII-UHFFFAOYSA-N N-cyclopentyl-5-[2-[[5-[(4-ethylpiperazin-1-yl)methyl]pyridin-2-yl]amino]-5-fluoropyrimidin-4-yl]-4-methyl-1,3-thiazol-2-amine Chemical compound C1(CCCC1)NC=1SC(=C(N=1)C)C1=NC(=NC=C1F)NC1=NC=C(C=C1)CN1CCN(CC1)CC POFVJRKJJBFPII-UHFFFAOYSA-N 0.000 claims description 5
- YATJQLMEBIHACT-UHFFFAOYSA-N [2-chloro-4-(2,4-difluoroanilino)phenyl]-[5-(3-hydroxybutylamino)-2-methylphenyl]methanone Chemical compound CC(O)CCNC1=CC=C(C)C(C(=O)C=2C(=CC(NC=3C(=CC(F)=CC=3)F)=CC=2)Cl)=C1 YATJQLMEBIHACT-UHFFFAOYSA-N 0.000 claims description 5
- CFCDICLFWSVQOZ-UHFFFAOYSA-N [2-chloro-4-(2,4-difluoroanilino)phenyl]-[5-(3-hydroxyphenyl)-2-methylphenyl]methanone Chemical compound CC1=CC=C(C=2C=C(O)C=CC=2)C=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=C(F)C=C1F CFCDICLFWSVQOZ-UHFFFAOYSA-N 0.000 claims description 5
- HDUGGJHNNJMXTP-UHFFFAOYSA-N [2-chloro-4-(2,4-difluoroanilino)phenyl]-[5-(4-methoxyphenyl)-2-methylphenyl]methanone Chemical compound C1=CC(OC)=CC=C1C1=CC=C(C)C(C(=O)C=2C(=CC(NC=3C(=CC(F)=CC=3)F)=CC=2)Cl)=C1 HDUGGJHNNJMXTP-UHFFFAOYSA-N 0.000 claims description 5
- 239000003054 catalyst Substances 0.000 claims description 5
- IICLYCCTMMRTJU-UHFFFAOYSA-N ethyl 2-[[3-[2-chloro-4-(2,4-difluoroanilino)benzoyl]-4-methylbenzoyl]amino]acetate Chemical compound CCOC(=O)CNC(=O)C1=CC=C(C)C(C(=O)C=2C(=CC(NC=3C(=CC(F)=CC=3)F)=CC=2)Cl)=C1 IICLYCCTMMRTJU-UHFFFAOYSA-N 0.000 claims description 5
- PSLNYJZVMXBKLW-UHFFFAOYSA-N ethyl 2-[[3-[2-chloro-4-(2,4-difluoroanilino)benzoyl]-4-methylphenyl]carbamoylamino]acetate Chemical compound CCOC(=O)CNC(=O)NC1=CC=C(C)C(C(=O)C=2C(=CC(NC=3C(=CC(F)=CC=3)F)=CC=2)Cl)=C1 PSLNYJZVMXBKLW-UHFFFAOYSA-N 0.000 claims description 5
- YBHSFAYSXATAJM-UHFFFAOYSA-N ethyl 3-[[3-[2-chloro-4-(2,4-difluoroanilino)benzoyl]-4-methylphenyl]carbamoylamino]propanoate Chemical compound CCOC(=O)CCNC(=O)NC1=CC=C(C)C(C(=O)C=2C(=CC(NC=3C(=CC(F)=CC=3)F)=CC=2)Cl)=C1 YBHSFAYSXATAJM-UHFFFAOYSA-N 0.000 claims description 5
- WSFSSNUMVMOOMR-BJUDXGSMSA-N methanone Chemical compound O=[11CH2] WSFSSNUMVMOOMR-BJUDXGSMSA-N 0.000 claims description 5
- UXQWXUFWQRJKNV-UHFFFAOYSA-N methyl 2-[[3-[2-chloro-4-(2,4-difluoroanilino)benzoyl]-4-methylphenyl]carbamoylamino]benzoate Chemical compound COC(=O)C1=CC=CC=C1NC(=O)NC1=CC=C(C)C(C(=O)C=2C(=CC(NC=3C(=CC(F)=CC=3)F)=CC=2)Cl)=C1 UXQWXUFWQRJKNV-UHFFFAOYSA-N 0.000 claims description 5
- SFYNBPCWLINGFA-UHFFFAOYSA-N n-[3-[2-chloro-4-(2,4-difluoroanilino)benzoyl]-4-methylphenyl]-2-hydroxybenzamide Chemical compound C1=C(C(=O)C=2C(=CC(NC=3C(=CC(F)=CC=3)F)=CC=2)Cl)C(C)=CC=C1NC(=O)C1=CC=CC=C1O SFYNBPCWLINGFA-UHFFFAOYSA-N 0.000 claims description 5
- JLASJMGKTZFRHL-UHFFFAOYSA-N n-[3-[2-chloro-4-(2,4-difluoroanilino)benzoyl]-4-methylphenyl]-3-hydroxypropanamide Chemical compound CC1=CC=C(NC(=O)CCO)C=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=C(F)C=C1F JLASJMGKTZFRHL-UHFFFAOYSA-N 0.000 claims description 5
- CEFMDEVZSMEXCF-UHFFFAOYSA-N n-[3-[2-chloro-4-(2,4-difluoroanilino)benzoyl]-4-methylphenyl]-3-morpholin-4-ylpropanamide Chemical compound C1=C(C(=O)C=2C(=CC(NC=3C(=CC(F)=CC=3)F)=CC=2)Cl)C(C)=CC=C1NC(=O)CCN1CCOCC1 CEFMDEVZSMEXCF-UHFFFAOYSA-N 0.000 claims description 5
- ARRCKKQUPUEHGA-UHFFFAOYSA-N n-[3-[2-chloro-4-(2,4-difluoroanilino)benzoyl]-4-methylphenyl]propanamide Chemical compound CCC(=O)NC1=CC=C(C)C(C(=O)C=2C(=CC(NC=3C(=CC(F)=CC=3)F)=CC=2)Cl)=C1 ARRCKKQUPUEHGA-UHFFFAOYSA-N 0.000 claims description 5
- KUOVLNPBYWWCLW-UHFFFAOYSA-N 1-[3-[2-chloro-4-(2,4-difluoroanilino)benzoyl]-4-methylphenyl]-3-phenylurea Chemical compound C1=C(C(=O)C=2C(=CC(NC=3C(=CC(F)=CC=3)F)=CC=2)Cl)C(C)=CC=C1NC(=O)NC1=CC=CC=C1 KUOVLNPBYWWCLW-UHFFFAOYSA-N 0.000 claims description 4
- OYMWQACNUFJIPM-UHFFFAOYSA-N 1-benzyl-3-[3-[2-chloro-4-(2,4-difluoroanilino)benzoyl]-4-methylphenyl]urea Chemical compound C1=C(C(=O)C=2C(=CC(NC=3C(=CC(F)=CC=3)F)=CC=2)Cl)C(C)=CC=C1NC(=O)NCC1=CC=CC=C1 OYMWQACNUFJIPM-UHFFFAOYSA-N 0.000 claims description 4
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- LAUADXJKOMGFRB-UHFFFAOYSA-N 3-(4-anilino-2-chlorobenzoyl)-n-(2,2-difluoroethyl)-4-methoxybenzamide Chemical compound COC1=CC=C(C(=O)NCC(F)F)C=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1 LAUADXJKOMGFRB-UHFFFAOYSA-N 0.000 claims description 4
- SKMKJBYBPYBDMN-RYUDHWBXSA-N 3-(difluoromethoxy)-5-[2-(3,3-difluoropyrrolidin-1-yl)-6-[(1s,4s)-2-oxa-5-azabicyclo[2.2.1]heptan-5-yl]pyrimidin-4-yl]pyridin-2-amine Chemical compound C1=C(OC(F)F)C(N)=NC=C1C1=CC(N2[C@H]3C[C@H](OC3)C2)=NC(N2CC(F)(F)CC2)=N1 SKMKJBYBPYBDMN-RYUDHWBXSA-N 0.000 claims description 4
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- FVEDXXPVSCVQFB-UHFFFAOYSA-N 3-[2-chloro-4-(4-chloro-2-fluoroanilino)benzoyl]-n-[2-(dimethylamino)ethyl]-4-methylbenzamide Chemical compound CN(C)CCNC(=O)C1=CC=C(C)C(C(=O)C=2C(=CC(NC=3C(=CC(Cl)=CC=3)F)=CC=2)Cl)=C1 FVEDXXPVSCVQFB-UHFFFAOYSA-N 0.000 claims description 4
- IJRKLHTZAIFUTB-UHFFFAOYSA-N 5-nitro-2-(2-phenylethylamino)benzoic acid Chemical compound OC(=O)C1=CC([N+]([O-])=O)=CC=C1NCCC1=CC=CC=C1 IJRKLHTZAIFUTB-UHFFFAOYSA-N 0.000 claims description 4
- QBYJBZPUGVGKQQ-SJJAEHHWSA-N aldrin Chemical compound C1[C@H]2C=C[C@@H]1[C@H]1[C@@](C3(Cl)Cl)(Cl)C(Cl)=C(Cl)[C@@]3(Cl)[C@H]12 QBYJBZPUGVGKQQ-SJJAEHHWSA-N 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- DFBKLUNHFCTMDC-GKRDHZSOSA-N endrin Chemical compound C([C@@H]1[C@H]2[C@@]3(Cl)C(Cl)=C([C@]([C@H]22)(Cl)C3(Cl)Cl)Cl)[C@@H]2[C@H]2[C@@H]1O2 DFBKLUNHFCTMDC-GKRDHZSOSA-N 0.000 claims description 4
- 125000002757 morpholinyl group Chemical group 0.000 claims description 4
- UBSMCSQYJPNCIS-UHFFFAOYSA-N n-(2-amino-2-oxoethyl)-3-[2-chloro-4-(4-fluoroanilino)benzoyl]-4-methoxybenzamide Chemical compound COC1=CC=C(C(=O)NCC(N)=O)C=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=C(F)C=C1 UBSMCSQYJPNCIS-UHFFFAOYSA-N 0.000 claims description 4
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 4
- NQPVSRMRAFCRFE-UHFFFAOYSA-N 1-[3-[2-chloro-4-(2,4-difluoroanilino)benzoyl]-4-methylphenyl]-3-ethylurea Chemical compound CCNC(=O)NC1=CC=C(C)C(C(=O)C=2C(=CC(NC=3C(=CC(F)=CC=3)F)=CC=2)Cl)=C1 NQPVSRMRAFCRFE-UHFFFAOYSA-N 0.000 claims description 3
- FOOZQYBYDMJUMM-UHFFFAOYSA-N 1-[3-[2-chloro-4-(2,4-difluoroanilino)benzoyl]-4-methylphenyl]-3-propylurea Chemical compound CCCNC(=O)NC1=CC=C(C)C(C(=O)C=2C(=CC(NC=3C(=CC(F)=CC=3)F)=CC=2)Cl)=C1 FOOZQYBYDMJUMM-UHFFFAOYSA-N 0.000 claims description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 3
- DTMPNPNDBYWFSL-UHFFFAOYSA-N 3-[2-chloro-4-(2,4-difluoroanilino)benzoyl]-n-(2,3-dihydroxypropyl)-4-methoxybenzamide Chemical compound COC1=CC=C(C(=O)NCC(O)CO)C=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=C(F)C=C1F DTMPNPNDBYWFSL-UHFFFAOYSA-N 0.000 claims description 3
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- VXRCYWUDCZVSNU-UHFFFAOYSA-N 3-[2-chloro-4-(2,4-difluoroanilino)benzoyl]-n-(2-hydroxypropyl)-4-methylbenzamide Chemical compound CC(O)CNC(=O)C1=CC=C(C)C(C(=O)C=2C(=CC(NC=3C(=CC(F)=CC=3)F)=CC=2)Cl)=C1 VXRCYWUDCZVSNU-UHFFFAOYSA-N 0.000 claims description 3
- CUBFNDVOJWGDMZ-UHFFFAOYSA-N 3-[2-chloro-4-(2,4-difluoroanilino)benzoyl]-n-(cyclohexylmethyl)-4-methylbenzamide Chemical compound CC1=CC=C(C(=O)NCC2CCCCC2)C=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=C(F)C=C1F CUBFNDVOJWGDMZ-UHFFFAOYSA-N 0.000 claims description 3
- FDEXQNUAEVLETR-UHFFFAOYSA-N 3-[2-chloro-4-(4-chloro-2-fluoroanilino)benzoyl]-4-methyl-n-(2-methylpropyl)benzamide Chemical compound CC(C)CNC(=O)C1=CC=C(C)C(C(=O)C=2C(=CC(NC=3C(=CC(Cl)=CC=3)F)=CC=2)Cl)=C1 FDEXQNUAEVLETR-UHFFFAOYSA-N 0.000 claims description 3
- AYDPKVPZDYUGET-UHFFFAOYSA-N 3-[2-chloro-4-(4-chloro-2-fluoroanilino)benzoyl]-n-(3-methoxypropyl)-4-methylbenzamide Chemical compound COCCCNC(=O)C1=CC=C(C)C(C(=O)C=2C(=CC(NC=3C(=CC(Cl)=CC=3)F)=CC=2)Cl)=C1 AYDPKVPZDYUGET-UHFFFAOYSA-N 0.000 claims description 3
- JPZYCWDJVNWEFN-UHFFFAOYSA-N 3-[4-(2-aminoanilino)-2-chlorobenzoyl]-n-(2-hydroxyethyl)-4-methylbenzamide Chemical compound CC1=CC=C(C(=O)NCCO)C=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1N JPZYCWDJVNWEFN-UHFFFAOYSA-N 0.000 claims description 3
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Classifications
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- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
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- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
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- C07D263/14—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with radicals substituted by oxygen atoms
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- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
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- C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
-
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- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
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- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no 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
- C07D309/10—Oxygen atoms
- C07D309/12—Oxygen atoms only hydrogen atoms and one oxygen atom directly attached to ring carbon atoms, e.g. tetrahydropyranyl ethers
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- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/18—Radicals substituted by singly bound oxygen or sulfur atoms
- C07D317/22—Radicals substituted by singly bound oxygen or sulfur atoms etherified
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom 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
- C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
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| MX2007001215A (es) | 2004-08-06 | 2007-04-17 | Otsuka Pharma Co Ltd | Compuestos aromaticos. |
| KR101260236B1 (ko) * | 2004-12-13 | 2013-05-06 | 레오 파마 에이/에스 | 트리아졸 치환된 아미노벤조페논 화합물 |
| KR101411167B1 (ko) | 2005-04-13 | 2014-06-23 | 아스텍스 테라퓨틱스 리미티드 | 하이드록시벤즈아미드 유도체 및 hsp90 억제제로서의이의 용도 |
| KR20080042170A (ko) * | 2005-09-07 | 2008-05-14 | 플렉시콘, 인코퍼레이티드 | Ppar 활성 화합물 |
| MY146514A (en) | 2005-12-05 | 2012-08-15 | Otsuka Pharma Co Ltd | Diarylether derivatives as antitumor agents |
| ATE545637T1 (de) * | 2005-12-15 | 2012-03-15 | Astrazeneca Ab | Substituierte diphenylether, -amine, -sulfide und methane zur behandlung von atemwegserkrankungen |
| US7754725B2 (en) | 2006-03-01 | 2010-07-13 | Astex Therapeutics Ltd. | Dihydroxyphenyl isoindolymethanones |
| KR100932093B1 (ko) | 2006-09-27 | 2009-12-16 | 주식회사종근당 | 미세소관 형성 저해제로서 유용한 벤조페논 유도체 |
| UA95978C2 (ru) | 2006-10-02 | 2011-09-26 | Оцука Фармас'Ютікел Ко., Лтд. | Ингибитор активации stat3/5 |
| EP2073802A1 (en) | 2006-10-12 | 2009-07-01 | Astex Therapeutics Limited | Pharmaceutical combinations |
| JP5528807B2 (ja) | 2006-10-12 | 2014-06-25 | アステックス、セラピューティックス、リミテッド | 複合薬剤 |
| WO2008044041A1 (en) | 2006-10-12 | 2008-04-17 | Astex Therapeutics Limited | Pharmaceutical combinations |
| GB0620259D0 (en) | 2006-10-12 | 2006-11-22 | Astex Therapeutics Ltd | Pharmaceutical compounds |
| JP5518478B2 (ja) | 2006-10-12 | 2014-06-11 | アステックス、セラピューティックス、リミテッド | 医薬化合物 |
| DK2272845T3 (en) | 2008-03-26 | 2015-05-04 | Chong Kun Dang Pharm Corp | Benzophenone Thiazole Derivatives for Inhibiting Microtubule Formation and Method for Preparation thereof |
| GB0806527D0 (en) | 2008-04-11 | 2008-05-14 | Astex Therapeutics Ltd | Pharmaceutical compounds |
| AU2009330686B2 (en) | 2008-06-16 | 2014-07-03 | The Ohio State University Research Foundation | Compounds for the treatment of cancer |
| US9447049B2 (en) | 2010-03-01 | 2016-09-20 | University Of Tennessee Research Foundation | Compounds for treatment of cancer |
| US9029408B2 (en) | 2008-06-16 | 2015-05-12 | Gtx, Inc. | Compounds for treatment of cancer |
| US8822513B2 (en) | 2010-03-01 | 2014-09-02 | Gtx, Inc. | Compounds for treatment of cancer |
| EP2330894B8 (en) | 2008-09-03 | 2017-04-19 | BioMarin Pharmaceutical Inc. | Compositions including 6-aminohexanoic acid derivatives as hdac inhibitors |
| MX2012007234A (es) | 2009-12-22 | 2012-07-30 | Leo Pharma As | Nanocristales de monohidrato de calciprotiol. |
| NZ601001A (en) | 2009-12-22 | 2014-07-25 | Leo Pharma As | Pharmaceutical composition comprising solvent mixture and a vitamin d derivative or analogue |
| BR112012015433B8 (pt) | 2009-12-22 | 2020-03-03 | Leo Pharma As | composição farmacêutica substancialmente anidra para aplicação cutânea |
| US8912184B1 (en) | 2010-03-01 | 2014-12-16 | Alzheimer's Institute Of America, Inc. | Therapeutic and diagnostic methods |
| MX2012010115A (es) | 2010-03-01 | 2013-02-26 | Gtx Inc | Compuestos para el tratamiento de cancer. |
| US10059723B2 (en) | 2011-02-28 | 2018-08-28 | Biomarin Pharmaceutical Inc. | Histone deacetylase inhibitors |
| US8957066B2 (en) | 2011-02-28 | 2015-02-17 | Biomarin Pharmaceutical Inc. | Histone deacetylase inhibitors |
| US9540395B2 (en) | 2011-02-28 | 2017-01-10 | Biomarin Pharmaceutical Inc. | Histone deacetylase inhibitors |
| TW201329025A (zh) | 2011-11-01 | 2013-07-16 | Astex Therapeutics Ltd | 醫藥化合物 |
| KR101229365B1 (ko) * | 2012-07-02 | 2013-02-18 | 대한민국 | 〔z〕n〔3〔2,4디플루오로페닐아미노〕1〔4나이트로페닐〕3옥소프로프1엔2일〕2메톡시벤즈아마이드를 유효성분으로 함유하는 신경퇴행성 질환 예방 및 치료용 약학적 조성물 |
| WO2014143666A1 (en) | 2013-03-15 | 2014-09-18 | Biomarin Pharmaceutical Inc. | Hdac inhibitors |
| CN103926794B (zh) * | 2014-04-29 | 2017-11-14 | 常州强力电子新材料股份有限公司 | 一种含有二苯甲酮衍生物光引发剂的光固化组合物 |
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| WO1998032730A1 (en) * | 1997-01-24 | 1998-07-30 | Leo Pharmaceutical Products Ltd. A/S (Løvens Kemiske Fabrik Produktionsaktieselskab) | Aminobenzophenones as inhibitors of interleukin and tnf |
| WO2001005746A1 (en) * | 1999-07-16 | 2001-01-25 | Leo Pharmaceutical Products Ltd. A/S (Løvens Kemiske Fabrik Produktionsaktieselskab) | AMINOBENZOPHENONES AS INHIBITORS OF IL-1β AND TNF-$g(a) |
| WO2001005745A1 (en) * | 1999-07-16 | 2001-01-25 | Leo Pharmaceutical Products Ltd. A/S (Løvens Kemiske Fabrik Produktionsaktieselskab) | AMINOBENZOPHENONES AS INHIBITORS OF IL-1β AND TNF-$g(a) |
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| WO2001005751A1 (en) * | 1999-07-16 | 2001-01-25 | Leo Pharmaceutical Products Ltd. A/S (Løvens Kemiske Fabrik Produktionsaktieselskab) | AMINOBENZOPHENONES AS INHIBITORS OF IL-1β AND TNF-$g(a) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| RU2240995C2 (ru) | 1999-07-16 | 2004-11-27 | Лео Фармасьютикал Продактс Лтд.А/С (Левенс Кемиске Фабрик Продукционсактиесельскаб) | Аминобензофеноны в качестве ингибиторов интерлейкина il-1бета и фактора некроза опухолей tnf-альфа |
| JP2004501191A (ja) * | 2000-06-28 | 2004-01-15 | テバ ファーマシューティカル インダストリーズ リミティド | カルベジロール |
| US20020165286A1 (en) | 2000-12-08 | 2002-11-07 | Hanne Hedeman | Dermal anti-inflammatory composition |
| KR100896667B1 (ko) * | 2001-08-28 | 2009-05-14 | 레오 파마 에이/에스 | 신규한 아미노벤조페논 및 이를 포함하는 약제학적 조성물 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998032730A1 (en) * | 1997-01-24 | 1998-07-30 | Leo Pharmaceutical Products Ltd. A/S (Løvens Kemiske Fabrik Produktionsaktieselskab) | Aminobenzophenones as inhibitors of interleukin and tnf |
| WO2001005746A1 (en) * | 1999-07-16 | 2001-01-25 | Leo Pharmaceutical Products Ltd. A/S (Løvens Kemiske Fabrik Produktionsaktieselskab) | AMINOBENZOPHENONES AS INHIBITORS OF IL-1β AND TNF-$g(a) |
| WO2001005745A1 (en) * | 1999-07-16 | 2001-01-25 | Leo Pharmaceutical Products Ltd. A/S (Løvens Kemiske Fabrik Produktionsaktieselskab) | AMINOBENZOPHENONES AS INHIBITORS OF IL-1β AND TNF-$g(a) |
| WO2001005744A1 (en) * | 1999-07-16 | 2001-01-25 | Leo Pharmaceutical Products Ltd. A/S (Løvens Kemiske Fabrik Produktionsaktieselskab) | Novel aminobenzophenones |
| WO2001005751A1 (en) * | 1999-07-16 | 2001-01-25 | Leo Pharmaceutical Products Ltd. A/S (Løvens Kemiske Fabrik Produktionsaktieselskab) | AMINOBENZOPHENONES AS INHIBITORS OF IL-1β AND TNF-$g(a) |
| WO2001042189A1 (en) * | 1999-12-06 | 2001-06-14 | Leo Pharma A/S | AMINOBENZOPHENONES AS INHIBITORS OF IL-1β AND TNF-$g(a) |
| WO2002076447A1 (en) * | 2001-03-23 | 2002-10-03 | Novartis Ag | Hallogenated aminobenzophenones and aminobenzoylpyridines as inhibitors of il-1 and tnf |
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