HRP20100225T1 - Spojevi aminobenzofenona supstituirani triazolom - Google Patents
Spojevi aminobenzofenona supstituirani triazolom Download PDFInfo
- Publication number
- HRP20100225T1 HRP20100225T1 HR20100225T HRP20100225T HRP20100225T1 HR P20100225 T1 HRP20100225 T1 HR P20100225T1 HR 20100225 T HR20100225 T HR 20100225T HR P20100225 T HRP20100225 T HR P20100225T HR P20100225 T1 HRP20100225 T1 HR P20100225T1
- Authority
- HR
- Croatia
- Prior art keywords
- phenyl
- methyl
- compound
- chloro
- triazol
- 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 1
- 125000001425 triazolyl group Chemical group 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract 79
- -1 C1-6amino Chemical group 0.000 claims abstract 64
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 15
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 14
- 239000001257 hydrogen Substances 0.000 claims abstract 14
- 229910052736 halogen Inorganic materials 0.000 claims abstract 12
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract 11
- 125000001424 substituent group Chemical group 0.000 claims abstract 11
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract 11
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract 10
- 125000004043 oxo group Chemical group O=* 0.000 claims abstract 9
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims abstract 8
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract 8
- 150000002367 halogens Chemical group 0.000 claims abstract 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract 6
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims abstract 5
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract 5
- 125000004760 (C1-C4) alkylsulfonylamino group Chemical group 0.000 claims abstract 4
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract 4
- 125000004758 (C1-C4) alkoxyimino group Chemical group 0.000 claims abstract 3
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims abstract 3
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims abstract 3
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims abstract 3
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract 3
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims abstract 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract 3
- 150000003839 salts Chemical class 0.000 claims abstract 3
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims abstract 3
- PSAGVOBYEMLIOJ-UHFFFAOYSA-N [4-(2-aminoanilino)-2-chlorophenyl]-[5-[1-(2-hydroxyethyl)triazol-4-yl]-2-methylphenyl]methanone Chemical compound CC1=CC=C(C=2N=NN(CCO)C=2)C=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1N PSAGVOBYEMLIOJ-UHFFFAOYSA-N 0.000 claims abstract 2
- 125000001246 bromo group Chemical group Br* 0.000 claims abstract 2
- 150000002431 hydrogen Chemical class 0.000 claims 9
- 239000003814 drug Substances 0.000 claims 4
- 125000005843 halogen group Chemical group 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
- 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 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 108010003541 Platelet Activating Factor Proteins 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- 229940079593 drug Drugs 0.000 claims 3
- 208000027866 inflammatory disease Diseases 0.000 claims 3
- 238000011282 treatment Methods 0.000 claims 3
- 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 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 2
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims 2
- IPSLCPYQZBVIEN-UHFFFAOYSA-N 1-[3-[2-chloro-4-(2,4-difluoroanilino)benzoyl]-4-methylphenyl]triazole-4-carboxylic acid Chemical compound CC1=CC=C(N2N=NC(=C2)C(O)=O)C=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=C(F)C=C1F IPSLCPYQZBVIEN-UHFFFAOYSA-N 0.000 claims 2
- LAIYTIHHGUHOFI-UHFFFAOYSA-N 2-[4-[3-[2-chloro-4-(2,4-difluoroanilino)benzoyl]-4-methylphenyl]triazol-1-yl]acetic acid Chemical compound CC1=CC=C(C=2N=NN(CC(O)=O)C=2)C=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=C(F)C=C1F LAIYTIHHGUHOFI-UHFFFAOYSA-N 0.000 claims 2
- SQVNITZYWXMWOG-UHFFFAOYSA-N 2-cyclohexyl-1-(2-methylquinolin-4-yl)-3-(1,3-thiazol-2-yl)guanidine Chemical compound C=12C=CC=CC2=NC(C)=CC=1NC(=NC1CCCCC1)NC1=NC=CS1 SQVNITZYWXMWOG-UHFFFAOYSA-N 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
- 125000003830 C1- C4 alkylcarbonylamino group Chemical group 0.000 claims 2
- 229940121948 Muscarinic receptor antagonist Drugs 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
- 206010028980 Neoplasm 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
- QYLUMBISWNPGQD-UHFFFAOYSA-N [2-chloro-4-(2,4-difluoroanilino)phenyl]-[5-[1-(2-chloroethyl)triazol-4-yl]-2-methylphenyl]methanone Chemical compound CC1=CC=C(C=2N=NN(CCCl)C=2)C=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=C(F)C=C1F QYLUMBISWNPGQD-UHFFFAOYSA-N 0.000 claims 2
- NJOOGIYDTAKFBC-UHFFFAOYSA-N [2-chloro-4-(2,5-difluoroanilino)phenyl]-[5-[4-(2-hydroxyethyl)triazol-1-yl]-2-methylphenyl]methanone Chemical compound CC1=CC=C(N2N=NC(CCO)=C2)C=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC(F)=CC=C1F NJOOGIYDTAKFBC-UHFFFAOYSA-N 0.000 claims 2
- 239000000464 adrenergic agent Substances 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 2
- 125000005194 alkoxycarbonyloxy group Chemical group 0.000 claims 2
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims 2
- 125000000217 alkyl group Chemical group 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
- 201000011510 cancer Diseases 0.000 claims 2
- 239000000812 cholinergic antagonist Substances 0.000 claims 2
- 229940067594 flufenamate Drugs 0.000 claims 2
- 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 2
- 239000003862 glucocorticoid Substances 0.000 claims 2
- 150000002343 gold Chemical class 0.000 claims 2
- 229960000905 indomethacin Drugs 0.000 claims 2
- 230000002757 inflammatory effect Effects 0.000 claims 2
- 208000002780 macular degeneration Diseases 0.000 claims 2
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 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
- 229960001639 penicillamine Drugs 0.000 claims 2
- 150000003873 salicylate salts Chemical class 0.000 claims 2
- 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 2
- 229960001940 sulfasalazine Drugs 0.000 claims 2
- 229940037128 systemic glucocorticoids Drugs 0.000 claims 2
- 229950006828 timegadine 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
- 150000003751 zinc Chemical class 0.000 claims 2
- QOXLRDHLLWKQCS-UHFFFAOYSA-N (4-anilino-2-methylphenyl)-[5-[4-(2-hydroxyethyl)triazol-1-yl]-2-methylphenyl]methanone Chemical compound CC1=CC=C(N2N=NC(CCO)=C2)C=C1C(=O)C(C(=C1)C)=CC=C1NC1=CC=CC=C1 QOXLRDHLLWKQCS-UHFFFAOYSA-N 0.000 claims 1
- OIIOPWHTJZYKIL-PMACEKPBSA-N (5S)-5-[[[5-[2-chloro-3-[2-chloro-3-[6-methoxy-5-[[[(2S)-5-oxopyrrolidin-2-yl]methylamino]methyl]pyrazin-2-yl]phenyl]phenyl]-3-methoxypyrazin-2-yl]methylamino]methyl]pyrrolidin-2-one Chemical compound C1(=C(N=C(C2=C(C(C3=CC=CC(=C3Cl)C3=NC(OC)=C(N=C3)CNC[C@H]3NC(=O)CC3)=CC=C2)Cl)C=N1)OC)CNC[C@H]1NC(=O)CC1 OIIOPWHTJZYKIL-PMACEKPBSA-N 0.000 claims 1
- MHHRCJOVAUOREJ-UHFFFAOYSA-N 1-[1-[3-[2-chloro-4-(2,4-difluoroanilino)benzoyl]-4-methylphenyl]triazol-4-yl]ethanone Chemical compound N1=NC(C(=O)C)=CN1C1=CC=C(C)C(C(=O)C=2C(=CC(NC=3C(=CC(F)=CC=3)F)=CC=2)Cl)=C1 MHHRCJOVAUOREJ-UHFFFAOYSA-N 0.000 claims 1
- QNFUCLGUCMVXLS-UHFFFAOYSA-N 1-[3-[4-[5-[4-(2-hydroxyethyl)triazol-1-yl]-2-methylbenzoyl]-3-methylanilino]phenyl]ethanone Chemical compound CC(=O)C1=CC=CC(NC=2C=C(C)C(C(=O)C=3C(=CC=C(C=3)N3N=NC(CCO)=C3)C)=CC=2)=C1 QNFUCLGUCMVXLS-UHFFFAOYSA-N 0.000 claims 1
- KYWXRBNOYGGPIZ-UHFFFAOYSA-N 1-morpholin-4-ylethanone Chemical compound CC(=O)N1CCOCC1 KYWXRBNOYGGPIZ-UHFFFAOYSA-N 0.000 claims 1
- LNWWQYYLZVZXKS-UHFFFAOYSA-N 1-pyrrolidin-1-ylethanone Chemical compound CC(=O)N1CCCC1 LNWWQYYLZVZXKS-UHFFFAOYSA-N 0.000 claims 1
- FVFPYAZLMFSPBO-UHFFFAOYSA-N 2-[4-[3-[2-chloro-4-(2,4-difluoroanilino)benzoyl]-4-methylphenyl]triazol-1-yl]-1-pyrrolidin-1-ylethanone Chemical compound CC1=CC=C(C=2N=NN(CC(=O)N3CCCC3)C=2)C=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=C(F)C=C1F FVFPYAZLMFSPBO-UHFFFAOYSA-N 0.000 claims 1
- HDKFHOSJUUBGOP-UHFFFAOYSA-N 2-[4-[3-[2-chloro-4-(2,4-difluoroanilino)benzoyl]-4-methylphenyl]triazol-1-yl]-n-(1-hydroxy-2-methylpropan-2-yl)acetamide Chemical compound CC1=CC=C(C=2N=NN(CC(=O)NC(C)(C)CO)C=2)C=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=C(F)C=C1F HDKFHOSJUUBGOP-UHFFFAOYSA-N 0.000 claims 1
- ARLQDESCSJFIKZ-UHFFFAOYSA-N 2-[4-[3-[2-chloro-4-(2,4-difluoroanilino)benzoyl]-4-methylphenyl]triazol-1-yl]-n-ethylacetamide Chemical compound N1=NN(CC(=O)NCC)C=C1C1=CC=C(C)C(C(=O)C=2C(=CC(NC=3C(=CC(F)=CC=3)F)=CC=2)Cl)=C1 ARLQDESCSJFIKZ-UHFFFAOYSA-N 0.000 claims 1
- NMCHXLZOXQGDLH-UHFFFAOYSA-N 2-[4-[3-[2-chloro-4-(2,4-difluoroanilino)benzoyl]-4-methylphenyl]triazol-1-yl]acetamide Chemical compound CC1=CC=C(C=2N=NN(CC(N)=O)C=2)C=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=C(F)C=C1F NMCHXLZOXQGDLH-UHFFFAOYSA-N 0.000 claims 1
- ZCHFQUVQSBJNIO-UHFFFAOYSA-N 2-[4-[3-[2-chloro-4-(4-fluoroanilino)benzoyl]-4-methylphenyl]triazol-1-yl]acetamide Chemical compound CC1=CC=C(C=2N=NN(CC(N)=O)C=2)C=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=C(F)C=C1 ZCHFQUVQSBJNIO-UHFFFAOYSA-N 0.000 claims 1
- PAYROHWFGZADBR-UHFFFAOYSA-N 2-[[4-amino-5-(5-iodo-4-methoxy-2-propan-2-ylphenoxy)pyrimidin-2-yl]amino]propane-1,3-diol Chemical compound C1=C(I)C(OC)=CC(C(C)C)=C1OC1=CN=C(NC(CO)CO)N=C1N PAYROHWFGZADBR-UHFFFAOYSA-N 0.000 claims 1
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims 1
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 claims 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 1
- WFOVEDJTASPCIR-UHFFFAOYSA-N 3-[(4-methyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)methylamino]-n-[[2-(trifluoromethyl)phenyl]methyl]benzamide Chemical compound N=1N=C(C=2C=CN=CC=2)N(C)C=1CNC(C=1)=CC=CC=1C(=O)NCC1=CC=CC=C1C(F)(F)F WFOVEDJTASPCIR-UHFFFAOYSA-N 0.000 claims 1
- JONGVUCCUCDLIB-UHFFFAOYSA-N 3-[4-[5-[4-(2-hydroxyethyl)triazol-1-yl]-2-methylbenzoyl]-3-methylanilino]benzonitrile Chemical compound CC1=CC=C(N2N=NC(CCO)=C2)C=C1C(=O)C(C(=C1)C)=CC=C1NC1=CC=CC(C#N)=C1 JONGVUCCUCDLIB-UHFFFAOYSA-N 0.000 claims 1
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
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- 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 1
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- LIMFPAAAIVQRRD-BCGVJQADSA-N N-[2-[(3S,4R)-3-fluoro-4-methoxypiperidin-1-yl]pyrimidin-4-yl]-8-[(2R,3S)-2-methyl-3-(methylsulfonylmethyl)azetidin-1-yl]-5-propan-2-ylisoquinolin-3-amine Chemical compound F[C@H]1CN(CC[C@H]1OC)C1=NC=CC(=N1)NC=1N=CC2=C(C=CC(=C2C=1)C(C)C)N1[C@@H]([C@H](C1)CS(=O)(=O)C)C LIMFPAAAIVQRRD-BCGVJQADSA-N 0.000 claims 1
- 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 1
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- JJIORZUMCQHBGM-UHFFFAOYSA-N [1-[3-[2-chloro-4-(2,4-difluoroanilino)benzoyl]-4-methylphenyl]triazol-4-yl]methylurea Chemical compound CC1=CC=C(N2N=NC(CNC(N)=O)=C2)C=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=C(F)C=C1F JJIORZUMCQHBGM-UHFFFAOYSA-N 0.000 claims 1
- YPWNUKPWTQWGGT-UHFFFAOYSA-N [2-chloro-4-(2,3-dichloroanilino)phenyl]-[5-[4-(2-hydroxyethyl)triazol-1-yl]-2-methylphenyl]methanone Chemical compound CC1=CC=C(N2N=NC(CCO)=C2)C=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC(Cl)=C1Cl YPWNUKPWTQWGGT-UHFFFAOYSA-N 0.000 claims 1
- RVUJZPYOZZSQER-UHFFFAOYSA-N [2-chloro-4-(2,4-difluoroanilino)phenyl]-[2-chloro-5-[4-(2-hydroxyethyl)triazol-1-yl]phenyl]methanone Chemical compound N1=NC(CCO)=CN1C1=CC=C(Cl)C(C(=O)C=2C(=CC(NC=3C(=CC(F)=CC=3)F)=CC=2)Cl)=C1 RVUJZPYOZZSQER-UHFFFAOYSA-N 0.000 claims 1
- HPCBBGUVEPKSHM-UHFFFAOYSA-N [2-chloro-4-(2,4-difluoroanilino)phenyl]-[2-methoxy-5-[1-[2-(oxan-2-yloxy)ethyl]triazol-4-yl]phenyl]methanone Chemical compound COC1=CC=C(C=2N=NN(CCOC3OCCCC3)C=2)C=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=C(F)C=C1F HPCBBGUVEPKSHM-UHFFFAOYSA-N 0.000 claims 1
- FIYVERWJMSFMNU-UHFFFAOYSA-N [2-chloro-4-(2,4-difluoroanilino)phenyl]-[2-methyl-5-[1-[2-(oxan-2-yloxy)ethyl]triazol-4-yl]phenyl]methanone Chemical compound CC1=CC=C(C=2N=NN(CCOC3OCCCC3)C=2)C=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=C(F)C=C1F FIYVERWJMSFMNU-UHFFFAOYSA-N 0.000 claims 1
- IGMJGJQJHRWAAM-UHFFFAOYSA-N [2-chloro-4-(2,4-difluoroanilino)phenyl]-[2-methyl-5-[1-[3-(oxan-2-yloxy)propyl]triazol-4-yl]phenyl]methanone Chemical compound CC1=CC=C(C=2N=NN(CCCOC3OCCCC3)C=2)C=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=C(F)C=C1F IGMJGJQJHRWAAM-UHFFFAOYSA-N 0.000 claims 1
- ZGQCHLWCIGSBQJ-UHFFFAOYSA-N [2-chloro-4-(2,4-difluoroanilino)phenyl]-[2-methyl-5-[4-(2-morpholin-4-ylethyl)triazol-1-yl]phenyl]methanone Chemical compound CC1=CC=C(N2N=NC(CCN3CCOCC3)=C2)C=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=C(F)C=C1F ZGQCHLWCIGSBQJ-UHFFFAOYSA-N 0.000 claims 1
- YMTXGFBWCMBKIF-UHFFFAOYSA-N [2-chloro-4-(2,4-difluoroanilino)phenyl]-[2-methyl-5-[4-[2-(propylamino)ethyl]triazol-1-yl]phenyl]methanone Chemical compound N1=NC(CCNCCC)=CN1C1=CC=C(C)C(C(=O)C=2C(=CC(NC=3C(=CC(F)=CC=3)F)=CC=2)Cl)=C1 YMTXGFBWCMBKIF-UHFFFAOYSA-N 0.000 claims 1
- WPCMPKWKLMGGNX-UHFFFAOYSA-N [2-chloro-4-(2,4-difluoroanilino)phenyl]-[5-[1-(2,3-dihydroxypropyl)triazol-4-yl]-2-methylphenyl]methanone Chemical compound CC1=CC=C(C=2N=NN(CC(O)CO)C=2)C=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=C(F)C=C1F WPCMPKWKLMGGNX-UHFFFAOYSA-N 0.000 claims 1
- ASWLJVXFJYXYOB-UHFFFAOYSA-N [2-chloro-4-(2,4-difluoroanilino)phenyl]-[5-[1-(2-hydroxyethyl)triazol-4-yl]-2-methoxyphenyl]methanone Chemical compound COC1=CC=C(C=2N=NN(CCO)C=2)C=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=C(F)C=C1F ASWLJVXFJYXYOB-UHFFFAOYSA-N 0.000 claims 1
- GWCCLULZZNYMOB-UHFFFAOYSA-N [2-chloro-4-(2,4-difluoroanilino)phenyl]-[5-[1-(2-hydroxyethyl)triazol-4-yl]-2-methylphenyl]methanone Chemical compound CC1=CC=C(C=2N=NN(CCO)C=2)C=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=C(F)C=C1F GWCCLULZZNYMOB-UHFFFAOYSA-N 0.000 claims 1
- DQECINXXQNSECL-UHFFFAOYSA-N [2-chloro-4-(2,4-difluoroanilino)phenyl]-[5-[1-(3-hydroxypropyl)triazol-4-yl]-2-methylphenyl]methanone Chemical compound CC1=CC=C(C=2N=NN(CCCO)C=2)C=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=C(F)C=C1F DQECINXXQNSECL-UHFFFAOYSA-N 0.000 claims 1
- JFGDPZLUDYRXFI-UHFFFAOYSA-N [2-chloro-4-(2,4-difluoroanilino)phenyl]-[5-[1-[(2,2-dimethyl-1,3-dioxolan-4-yl)methyl]triazol-4-yl]-2-methylphenyl]methanone Chemical compound CC1=CC=C(C=2N=NN(CC3OC(C)(C)OC3)C=2)C=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=C(F)C=C1F JFGDPZLUDYRXFI-UHFFFAOYSA-N 0.000 claims 1
- UZEODWZESGZYPC-UHFFFAOYSA-N [2-chloro-4-(2,4-difluoroanilino)phenyl]-[5-[4-(2-hydroxyethyl)triazol-1-yl]-2-methylphenyl]methanone Chemical compound CC1=CC=C(N2N=NC(CCO)=C2)C=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=C(F)C=C1F UZEODWZESGZYPC-UHFFFAOYSA-N 0.000 claims 1
- IDOCEJVHXWDLIA-UHFFFAOYSA-N [2-chloro-4-(2,4-difluoroanilino)phenyl]-[5-[4-(2-hydroxypropan-2-yl)triazol-1-yl]-2-methylphenyl]methanone Chemical compound CC1=CC=C(N2N=NC(=C2)C(C)(C)O)C=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=C(F)C=C1F IDOCEJVHXWDLIA-UHFFFAOYSA-N 0.000 claims 1
- PVWZSYHVAHYQMT-UHFFFAOYSA-N [2-chloro-4-(2,4-difluoroanilino)phenyl]-[5-[4-(3-hydroxyprop-1-enyl)triazol-1-yl]-2-methylphenyl]methanone Chemical compound CC1=CC=C(N2N=NC(C=CCO)=C2)C=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=C(F)C=C1F PVWZSYHVAHYQMT-UHFFFAOYSA-N 0.000 claims 1
- GOQTTZHMKGKNCG-UHFFFAOYSA-N [2-chloro-4-(2,4-difluoroanilino)phenyl]-[5-[4-(hydroxymethyl)triazol-1-yl]-2-methylphenyl]methanone Chemical compound CC1=CC=C(N2N=NC(CO)=C2)C=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=C(F)C=C1F GOQTTZHMKGKNCG-UHFFFAOYSA-N 0.000 claims 1
- NDKMGYMBTPIZCL-UHFFFAOYSA-N [2-chloro-4-(2,4-difluoroanilino)phenyl]-[5-[4-[2-(2-hydroxyethylamino)ethyl]triazol-1-yl]-2-methylphenyl]methanone Chemical compound CC1=CC=C(N2N=NC(CCNCCO)=C2)C=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=C(F)C=C1F NDKMGYMBTPIZCL-UHFFFAOYSA-N 0.000 claims 1
- OMWQVGTYKQABBG-UHFFFAOYSA-N [2-chloro-4-(2,4-difluoroanilino)phenyl]-[5-[4-[2-(diethylamino)ethyl]triazol-1-yl]-2-methylphenyl]methanone Chemical compound N1=NC(CCN(CC)CC)=CN1C1=CC=C(C)C(C(=O)C=2C(=CC(NC=3C(=CC(F)=CC=3)F)=CC=2)Cl)=C1 OMWQVGTYKQABBG-UHFFFAOYSA-N 0.000 claims 1
- ALQHEMGFLAWGPP-UHFFFAOYSA-N [2-chloro-4-(2-chloro-4-fluoroanilino)phenyl]-[5-[4-(2-hydroxyethyl)triazol-1-yl]-2-methylphenyl]methanone Chemical compound CC1=CC=C(N2N=NC(CCO)=C2)C=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=C(F)C=C1Cl ALQHEMGFLAWGPP-UHFFFAOYSA-N 0.000 claims 1
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- UBDWJQOOFUKOJH-UHFFFAOYSA-N [2-chloro-4-(2-methylanilino)phenyl]-[5-[4-(2-hydroxyethyl)triazol-1-yl]-2-methylphenyl]methanone Chemical compound CC1=CC=CC=C1NC(C=C1Cl)=CC=C1C(=O)C1=CC(N2N=NC(CCO)=C2)=CC=C1C UBDWJQOOFUKOJH-UHFFFAOYSA-N 0.000 claims 1
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- OXPALBSSUDXDIH-UHFFFAOYSA-N [2-chloro-4-(3-chloroanilino)phenyl]-[5-[4-(2-hydroxyethyl)triazol-1-yl]-2-methylphenyl]methanone Chemical compound CC1=CC=C(N2N=NC(CCO)=C2)C=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC(Cl)=C1 OXPALBSSUDXDIH-UHFFFAOYSA-N 0.000 claims 1
- JDAYZUJMYGBGEL-UHFFFAOYSA-N [2-chloro-4-(3-fluoroanilino)phenyl]-[5-[4-(2-hydroxyethyl)triazol-1-yl]-2-methylphenyl]methanone Chemical compound CC1=CC=C(N2N=NC(CCO)=C2)C=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC(F)=C1 JDAYZUJMYGBGEL-UHFFFAOYSA-N 0.000 claims 1
- LCSOELIQNONKSF-UHFFFAOYSA-N [2-chloro-4-(3-methylanilino)phenyl]-[5-[4-(2-hydroxyethyl)triazol-1-yl]-2-methylphenyl]methanone Chemical compound CC1=CC=CC(NC=2C=C(Cl)C(C(=O)C=3C(=CC=C(C=3)N3N=NC(CCO)=C3)C)=CC=2)=C1 LCSOELIQNONKSF-UHFFFAOYSA-N 0.000 claims 1
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- QEONPKXGTKVONB-UHFFFAOYSA-N [2-chloro-4-(4-fluoro-2-methylanilino)phenyl]-[5-[4-(2-hydroxyethyl)triazol-1-yl]-2-methylphenyl]methanone Chemical compound CC1=CC(F)=CC=C1NC(C=C1Cl)=CC=C1C(=O)C1=CC(N2N=NC(CCO)=C2)=CC=C1C QEONPKXGTKVONB-UHFFFAOYSA-N 0.000 claims 1
- ZDJDCCYATQGIBA-UHFFFAOYSA-N [2-chloro-4-(4-fluoroanilino)phenyl]-[2-methyl-5-[1-[2-(oxan-2-yloxy)ethyl]triazol-4-yl]phenyl]methanone Chemical compound CC1=CC=C(C=2N=NN(CCOC3OCCCC3)C=2)C=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=C(F)C=C1 ZDJDCCYATQGIBA-UHFFFAOYSA-N 0.000 claims 1
- YQAFWTAZXJRIHF-UHFFFAOYSA-N [2-chloro-4-(4-fluoroanilino)phenyl]-[5-[1-(2,3-dihydroxypropyl)triazol-4-yl]-2-methylphenyl]methanone Chemical compound CC1=CC=C(C=2N=NN(CC(O)CO)C=2)C=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=C(F)C=C1 YQAFWTAZXJRIHF-UHFFFAOYSA-N 0.000 claims 1
- YEAWXBOYLLODEU-UHFFFAOYSA-N [2-chloro-4-(4-fluoroanilino)phenyl]-[5-[1-(2-hydroxyethyl)triazol-4-yl]-2-methylphenyl]methanone Chemical compound CC1=CC=C(C=2N=NN(CCO)C=2)C=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=C(F)C=C1 YEAWXBOYLLODEU-UHFFFAOYSA-N 0.000 claims 1
- DSOPEHVYPKJOIE-UHFFFAOYSA-N [2-chloro-4-(4-fluoroanilino)phenyl]-[5-[1-[(2,2-dimethyl-1,3-dioxolan-4-yl)methyl]triazol-4-yl]-2-methylphenyl]methanone Chemical compound CC1=CC=C(C=2N=NN(CC3OC(C)(C)OC3)C=2)C=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=C(F)C=C1 DSOPEHVYPKJOIE-UHFFFAOYSA-N 0.000 claims 1
- PGWSYCJRVZTWQT-UHFFFAOYSA-N [2-chloro-4-(4-fluoroanilino)phenyl]-[5-[4-(2-hydroxyethyl)triazol-1-yl]-2-methylphenyl]methanone Chemical compound CC1=CC=C(N2N=NC(CCO)=C2)C=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=C(F)C=C1 PGWSYCJRVZTWQT-UHFFFAOYSA-N 0.000 claims 1
- PCZRMNXKLHGJEI-UHFFFAOYSA-N [2-chloro-4-(4-methoxyanilino)phenyl]-[5-[4-(2-hydroxyethyl)triazol-1-yl]-2-methylphenyl]methanone Chemical compound C1=CC(OC)=CC=C1NC(C=C1Cl)=CC=C1C(=O)C1=CC(N2N=NC(CCO)=C2)=CC=C1C PCZRMNXKLHGJEI-UHFFFAOYSA-N 0.000 claims 1
- KZBMQQUTRIHXNF-UHFFFAOYSA-N [4-(2,4-difluoroanilino)-2-methylphenyl]-[5-[4-(2-hydroxyethyl)triazol-1-yl]-2-methylphenyl]methanone Chemical compound CC1=CC=C(N2N=NC(CCO)=C2)C=C1C(=O)C(C(=C1)C)=CC=C1NC1=CC=C(F)C=C1F KZBMQQUTRIHXNF-UHFFFAOYSA-N 0.000 claims 1
- KWYBRZXGQGBIQQ-UHFFFAOYSA-N [4-(3,4-dichloroanilino)-2-methylphenyl]-[5-[4-(2-hydroxyethyl)triazol-1-yl]-2-methylphenyl]methanone Chemical compound CC1=CC=C(N2N=NC(CCO)=C2)C=C1C(=O)C(C(=C1)C)=CC=C1NC1=CC=C(Cl)C(Cl)=C1 KWYBRZXGQGBIQQ-UHFFFAOYSA-N 0.000 claims 1
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- CUPNDHJHEMIQJW-UHFFFAOYSA-N [4-(3,4-dimethylanilino)-2-methylphenyl]-[5-[4-(2-hydroxyethyl)triazol-1-yl]-2-methylphenyl]methanone Chemical compound C1=C(C)C(C)=CC=C1NC(C=C1C)=CC=C1C(=O)C1=CC(N2N=NC(CCO)=C2)=CC=C1C CUPNDHJHEMIQJW-UHFFFAOYSA-N 0.000 claims 1
- NCIQWNXQHOBYCM-UHFFFAOYSA-N [4-(3-chloro-2-methylanilino)-2-methylphenyl]-[5-[4-(2-hydroxyethyl)triazol-1-yl]-2-methylphenyl]methanone Chemical compound CC1=CC=C(N2N=NC(CCO)=C2)C=C1C(=O)C(C(=C1)C)=CC=C1NC1=CC=CC(Cl)=C1C NCIQWNXQHOBYCM-UHFFFAOYSA-N 0.000 claims 1
- WVPHPBXDYSNARS-UHFFFAOYSA-N [4-(3-chloro-4-fluoroanilino)-2-methylphenyl]-[5-[4-(2-hydroxyethyl)triazol-1-yl]-2-methylphenyl]methanone Chemical compound CC1=CC=C(N2N=NC(CCO)=C2)C=C1C(=O)C(C(=C1)C)=CC=C1NC1=CC=C(F)C(Cl)=C1 WVPHPBXDYSNARS-UHFFFAOYSA-N 0.000 claims 1
- BKLIGHSWJYOTFB-UHFFFAOYSA-N [5-[4-(2-aminoethyl)triazol-1-yl]-2-methylphenyl]-[2-chloro-4-(2,4-difluoroanilino)phenyl]methanone Chemical compound CC1=CC=C(N2N=NC(CCN)=C2)C=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=C(F)C=C1F BKLIGHSWJYOTFB-UHFFFAOYSA-N 0.000 claims 1
- FLJGZIISKFQLIJ-UHFFFAOYSA-N [5-[4-(2-aminopropan-2-yl)triazol-1-yl]-2-methylphenyl]-[2-chloro-4-(2,4-difluoroanilino)phenyl]methanone Chemical compound CC1=CC=C(N2N=NC(=C2)C(C)(C)N)C=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=C(F)C=C1F FLJGZIISKFQLIJ-UHFFFAOYSA-N 0.000 claims 1
- STEAOSBDJJWHRR-UHFFFAOYSA-N [5-[4-(2-hydroxyethyl)triazol-1-yl]-2-methylphenyl]-[2-methyl-4-[3-(trifluoromethyl)anilino]phenyl]methanone Chemical compound CC1=CC=C(N2N=NC(CCO)=C2)C=C1C(=O)C(C(=C1)C)=CC=C1NC1=CC=CC(C(F)(F)F)=C1 STEAOSBDJJWHRR-UHFFFAOYSA-N 0.000 claims 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 1
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- 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 1
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- 206010003246 arthritis Diseases 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
- 201000008937 atopic dermatitis Diseases 0.000 claims 1
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims 1
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims 1
- 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 1
- 230000001684 chronic effect Effects 0.000 claims 1
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- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims 1
- 125000004494 ethyl ester group Chemical group 0.000 claims 1
- 208000030533 eye disease Diseases 0.000 claims 1
- 239000000945 filler Substances 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 1
- 230000004054 inflammatory process Effects 0.000 claims 1
- 150000004702 methyl esters Chemical class 0.000 claims 1
- XGEGHDBEHXKFPX-NJFSPNSNSA-N methylurea Chemical compound [14CH3]NC(N)=O XGEGHDBEHXKFPX-NJFSPNSNSA-N 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
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- HNMWZKCPBQXVCA-UHFFFAOYSA-N n-[2-[4-[3-[2-chloro-4-(2,4-difluoroanilino)benzoyl]-4-methylphenyl]triazol-1-yl]ethyl]methanesulfonamide Chemical compound CC1=CC=C(C=2N=NN(CCNS(C)(=O)=O)C=2)C=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=C(F)C=C1F HNMWZKCPBQXVCA-UHFFFAOYSA-N 0.000 claims 1
- GFDAJKLHBBMRGB-UHFFFAOYSA-N n-[3-[4-[5-[4-(2-hydroxyethyl)triazol-1-yl]-2-methylbenzoyl]-3-methylanilino]phenyl]acetamide Chemical compound CC(=O)NC1=CC=CC(NC=2C=C(C)C(C(=O)C=3C(=CC=C(C=3)N3N=NC(CCO)=C3)C)=CC=2)=C1 GFDAJKLHBBMRGB-UHFFFAOYSA-N 0.000 claims 1
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- 230000002265 prevention Effects 0.000 claims 1
- 230000002062 proliferating effect Effects 0.000 claims 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 claims 1
- 238000011321 prophylaxis Methods 0.000 claims 1
- 125000006235 propyl amino ethyl group Chemical group [H]N(C([H])([H])C([H])([H])*)C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
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- 210000002966 serum Anatomy 0.000 claims 1
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- KSAVQLQVUXSOCR-UHFFFAOYSA-M sodium lauroyl sarcosinate Chemical compound [Na+].CCCCCCCCCCCC(=O)N(C)CC([O-])=O KSAVQLQVUXSOCR-UHFFFAOYSA-M 0.000 claims 1
- 201000005671 spondyloarthropathy Diseases 0.000 claims 1
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- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/04—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles
- C07D249/06—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles with aryl radicals directly attached to ring atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
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Abstract
Spoj opće formule Ia ili Ibnaznačen time štoR1 je metil, kloro, bromo ili metoksi; R2 je kloro ili metil; R3 predstavlja C1-6alkil, C2-6alkenil, C2-6alkinil, C1-6hidroksialkil, C1-6haloalkil, C1-6alkoksi, C1-6alkoksikarbonil, C1-6amino, ureido, tioureido, C1-6alkilkarboniloksi, C1-6alkilkarbonil, C1-6alkoksikarboniloksi, C1-6alkoksisulfoniloksi, C1-6alkoksikarbamoil ili C1-6aminokarbonil, pri čemu je svaki od njih izborno supstituiran sa jednim ili više, istih ili različitih supstituenata izabranih iz grupe koju čine halogen, hidroksi, merkapto, trifluorometil, cijano, karboksi, CONH2, nitro, okso, -S(O)2NH2, C1-4alkil, C2-4alkenil, C2-4alkinil, C1-4hidroksialkil, C1-6haloalkil, C1-4alkoksi, C1-4alkoksikarbonil, ureido, tioureido, C1-4alkilkarboniloksi, C1-4alkoksikarboniloksi, C1-4alkoksisulfoniloksi, C1-4alkoksikarbamoil, C1-4aminokarbonil, C1-4alkiltio, C3-6cikloalkil, C3-6cikloalkenil, amino, imino, C1-4aminosulfonil, C1-4aminokarboniloksi, C1-4alkilsulfonilamino, C1-4alkoksiimino, C1-4alkilkarbonilamino, C1-4alkilsulfonil, C1-6heteroaril, C1-6heterocikloalkil ili C2-6heterocikloalkenil, pri čemu su navedeni C1-4alkil, C2-4alkenil, C2-4alkinil, C1-4hidroksialkil, C1-6haloalkil, C1-4alkoksi, C1-4alkoksikarbonil, ureido, tioureido, C1-4alkilkarboniloksi, C1-4alkoksikarboniloksi, C1-4alkoksisulfoniloksi, C1-4alkoksikarbamoil, C1-4aminokarbonil, C1-4alkiltio, C3-6cikloalkil, C3-C6cikloalkenil, amino, imino, C1-4aminosulfonil, C1-4aminokarboniloksi, C1-4alkilsulfonilamino, C1-4alkoksiimino, C1-4alkilkarbonilamino, C1-4alkilsulfonil, C1-6heteroaril, C1-6heterocikloalkil ili C2-6heterocikloalkenil, izborno dodatno supstituirani sa jednim ili više, istih ili različitih supstituenata izabranih iz grupe koju čine halogen, hidroksi, -NH2, merkapto, trifluorometil, cijano, karboksi, CONH2, nitro, okso, -S(O)2NH2, C1-4alkil ili C1-4hidroksialkil, ili R3 predstavlja vodik, hidroksi ili karboksi; R4, R5, R6, R7 i R8 međusobno nezavisno predstavljaju vodok, halogen, -NH2, hidroksi, trifluorometil, metoksi, etoksi, cijano, acetil, acetamido, metil ili etil; uz uvjet da spoj nije [4-(2-aminofenil)amino)-2-klorofenil]-[2-metil-5-[1-[2-[(tetrahidro-2H-piran-2-il)oksi]etil]-1H-1,2,3-triazol-4-il]-fenil]-metanon ili [4-[(2-aminofenil)amino]-2-klorofenil]-[5-[1-(2-hidroksietil)-1H-1,2,3-triazol-4-il]-2-metilfenil]-metanon; ili njegova farmaceutski prihvatljiva sol ili otopina. Patent sadrži još 25 patentnih zahtjeva.
Claims (26)
1. Spoj opće formule Ia ili Ib
[image]
[image]
naznačen time što
R1 je metil, kloro, bromo ili metoksi;
R2 je kloro ili metil;
R3 predstavlja C1-6alkil, C2-6alkenil, C2-6alkinil, C1-6hidroksialkil, C1-6haloalkil, C1-6alkoksi, C1-6alkoksikarbonil, C1-6amino, ureido, tioureido, C1-6alkilkarboniloksi, C1-6alkilkarbonil, C1-6alkoksikarboniloksi, C1-6alkoksisulfoniloksi, C1-6alkoksikarbamoil ili C1-6aminokarbonil,
pri čemu je svaki od njih izborno supstituiran sa jednim ili više, istih ili različitih supstituenata izabranih iz grupe koju čine halogen, hidroksi, merkapto, trifluorometil, cijano, karboksi, CONH2, nitro, okso, -S(O)2NH2, C1-4alkil, C2-4alkenil, C2-4alkinil, C1-4hidroksialkil, C1-6haloalkil, C1-4alkoksi, C1-4alkoksikarbonil, ureido, tioureido, C1-4alkilkarboniloksi, C1-4alkoksikarboniloksi, C1-4alkoksisulfoniloksi, C1-4alkoksikarbamoil, C1-4aminokarbonil, C1-4alkiltio, C3-6cikloalkil, C3-6cikloalkenil, amino, imino, C1-4aminosulfonil, C1-4aminokarboniloksi, C1-4alkilsulfonilamino, C1-4alkoksiimino, C1-4alkilkarbonilamino, C1-4alkilsulfonil, C1-6heteroaril, C1-6heterocikloalkil ili C2-6heterocikloalkenil,
pri čemu su navedeni C1-4alkil, C2-4alkenil, C2-4alkinil, C1-4hidroksialkil, C1-6haloalkil, C1-4alkoksi, C1-4alkoksikarbonil, ureido, tioureido, C1-4alkilkarboniloksi, C1-4alkoksikarboniloksi, C1-4alkoksisulfoniloksi, C1-4alkoksikarbamoil, C1-4aminokarbonil, C1-4alkiltio, C3-6cikloalkil, C3-C6cikloalkenil, amino, imino, C1-4aminosulfonil, C1-4aminokarboniloksi, C1-4alkilsulfonilamino, C1-4alkoksiimino, C1-4alkilkarbonilamino, C1-4alkilsulfonil, C1-6heteroaril, C1-6heterocikloalkil ili C2-6heterocikloalkenil, izborno dodatno supstituirani sa jednim ili više, istih ili različitih supstituenata izabranih iz grupe koju čine halogen, hidroksi, -NH2, merkapto, trifluorometil, cijano, karboksi, CONH2, nitro, okso, -S(O)2NH2, C1-4alkil ili C1-4hidroksialkil,
ili R3 predstavlja vodik, hidroksi ili karboksi;
R4, R5, R6, R7 i R8 međusobno nezavisno predstavljaju vodok, halogen, -NH2, hidroksi, trifluorometil, metoksi, etoksi, cijano, acetil, acetamido, metil ili etil;
uz uvjet da spoj nije [4-(2-aminofenil)amino)-2-klorofenil]-[2-metil-5-[1-[2-[(tetrahidro-2H-piran-2-il)oksi]etil]-1H-1,2,3-triazol-4-il]-fenil]-metanon ili [4-[(2-aminofenil)amino]-2-klorofenil]-[5-[1-(2-hidroksietil)-1H-1,2,3-triazol-4-il]-2-metilfenil]-metanon;
ili njegova farmaceutski prihvatljiva sol ili otopina.
2. Spoj prema patentnom zahtjevu 1, naznačen time što R3 predstavlja C1-6alkil, C2-6alkenil, C2-6alkinil, C1-6hidroksialkil, C1-6alkoksikarbonil, C1-6alkilkarbonil, ureido, ili C1-6aminokarbonil, pri čemu je svaki od njih izborno supstituiran sa jednim ili više, istih ili različitih supstituenata izabranih iz grupe koju čine halogen, hidroksi, merkapto, trifluorometil, cijano, karboksi, CONH2, nitro, okso, -S(O)2NH2, C1-4alkil, C2-4alkenil, C2-4alkinil, C1-4hidroksialkil, C1-4alkoksi, C1-4alkoksikarbonil, ureido, tioureido, C1-4alkilkarboniloksi, C1-4alkoksikarboniloksi, C1-4alkoksisulfoniloksi, C1-4alkoksikarbamoil, C1-4aminokarbonil, C1-4alkiltio, C3-6cikloalkil, C3-6cikloalkenil, amino, imino, C1-4aminosulfonil, C1-4aminokarboniloksi, C1-4alkilsulfonilamino, C1-4alkoksiimino, C1-4alkilkarbonilamino, C1-4alkilsulfonil, C1-6heteroaril, C1-6heterocikloalkil ili C2-6heterocikloalkenil, od kojih je 27 posljednjih izborno dalje supstituirano sa jednim ili više, istih ili različitih supstituenata izabranih iz grupe koju čine halogen, hidroksi, -NH2, merkapto, trifluorometil, cijano, karboksi, CONH2, nitro, okso, -S(O)2NH2, C1-4alkil ili C1-4hidroksialkil,
ili R3 predstavlja vodik, hidroksi ili karboksi.
3. Spoj prema patentnom zahtjevu 1 ili 2, naznačen time što R4, R5, R6, R7 i R8 međusobno nezavisno predstavljaju vodik, halogen, hidroksi, trifluorometil, metoksi, etoksi, metil ili etil.
4. Spoj prema patentnom zahtjevu 1 ili 2, naznačen time što R5, R6 i R7, međusobno nezavisno predstavljaju vodik, halogen, -NH2, hidroksi, trifluorometil, metoksi, etoksi, cijano, acetil, acetamido, metil ili etil, i pri čemu R4 i R8 međusobno nezavisno predstavljaju vodik, halogen, hidroksi, trifluorometil, metoksi, etoksi, cijano, acetil, acetamido, metil ili etil.
5. Spoj prema patentnom zahtjevu 1 ili 2, naznačen time što R4, R5, R6, R7 i R8 međusobno nezavisno predstavljaju vodik, fluoro ili kloro.
6. Spoj prema bilo kojem od patentnih zahtjeva 1-5, naznačen time što najmanje tri od R4, R5, R6, R7 ili R8 predstavljaju vodik.
7. Spoj prema bilo kojem od patentnih zahtjeva 1-6, naznačen time što R5, R7 i R8 predstavljaju vodik, ili što R5, R6, R7 i R8 predstavljaju vodik, ili što R4, R5, R7 i R8 predstavljaju vodik.
8. Spoj prema bilo kojem od patentnih zahtjeva 1-6, naznačen time što R4, R7 i R8, ili R6, R7 i R8, ili R4, R6, R7 i R8, ili R4, R6 i R8, ili R4, R6 i R7 predstavljaju vodik.
9. Spoj prema bilo kojem od patentnih zahtjeva 1-8, naznačen time što je R1 jednako metil i R2 je kloro.
10. Spoj prema bilo kojem od patentnih zahtjeva 1-9, naznačen time što R3 predstavlja C1-4alkil, C2-4alkenil ili C1-4hidroksialkil, pri čemu je svaki od njih izborno supstituiran sa jednim ili više, istih ili različitih supstituenata izabranih iz grupe koju čine halogen, hidroksi, merkapto, -NH2, karboksi, CONH2, nitro, okso, -S(O)2NH2, C1-2hidroksialkil, C1-2alkoksi, C1-2alkoksikarbonil, C1-2ureido, C1-2tioureido, C1-2alkilkarboniloksi, C1-2alkoksikarboniloksi, C1-2alkoksisulfoniloksi, C1-2alkoksikarbamoil, C1-2aminokarbonil, C1-2alkiltio, C1-2amino, C1-2imino, C1-2aminosulfonil, C1-2aminokarboniloksi, C1-2alkilsulfonilamino, C1-2alkoksiimino, C1-2alkilkarbonilamino, C1-2alkilsulfonil, C2-5heteroaril, C2-5heterocikloalkil, C3-5heterocikloalkenil, od kojih su posljednjih 22 izborno dodatno supstituirani sa jednim ili više, istih ili različitih supstituenata izabranih iz grupe koju čine hidroksi, -NH2, karboksi, CONH2, okso ili C1-3alkil.
11. Spoj prema bilo kojem od patentnih zahtjeva 1-10, naznačen time što R3 predstavlja C1-3alkil, C2-3alkenil ili C1-3hidroksialkil, pri čemu je svaki od njih izborno supstituiran sa jednim ili više, istih ili različitih supstituenata izabranih iz grupe koju čine hidroksi, -NH2, karboksi, kloro, CONCH2, okso, -S(O)2NH2, C1-2hidroksialkil, C1-2alkoksi, C1-2alkoksikarbonil, C0-2ureido, C1-2aminokarbonil, C1-2amino, C1-2alkilsulfonilamino, C2-5heterocikloalkil, od kojih su posljednjih 8 izborno dodatno supstituirani sa jednim ili više, istih ili različitih supstituenata izabranih iz grupe koju čine hidroksi ili C1-2alkil.
12. Spoj prema bilo kojem od patentnih zahtjeva 1-11, naznačen time što R3 predstavlja metil, etil, propil, propenil, gdje su svi oni supstituirani sa jednim, dva, tri ili četiri, ista ili različita supstituenta izabrana iz grupe koju čine hidroksi, CONH2, okso, dietilamino, etilaminokarbonil, metil, hidroksimetil, pirolidinil, morfolinil, kloro, H2N-C(O)-NH-, metoksikarbonil, metoksi, -NH2, etoksikarbonil, etoksi, metilsulfonilamino, -S(O)2NH2, tetrahidropiranil, [1,3]-dioksolanil, etilamino, piperazinil, pri čemu su posljednja četiri izborno supstituirani sa jednim, dva, tri ili četiri, ista ili različita supstituenta izabrana iz grupe koju čine metil ili etil.
13. Spoj prema bilo kojem od patentnih zahtjeva 1-12, naznačen time što je R3 jednako 2-hidroksietil, 3-hidroksipropil, karbamoilmetil, 2,3-dihidroksipropil, 2-(metilsulfonilamino)etil, sulfonilaminopropil, 2,2-dimetil-[1,3]dioksolan-4-ilmetil, 2-(tetrahidro-piran-2-iloksi)-etil, 3-(tetrahidro-piran-2-iloksi)-propil, etoksikarbonilmetil, karboksimetil, etilaminokarbonilmetil, (2-hidroksi-1,1-dimetil-etil)aminokarbonilmetil, 1-pirolidin-1-il-etanon, 1-morfolin-4-il-etanon, 2-kloroetil, 1-hidroksi-1-metil-etil, acetil, 1-amino-1-metil-etil, metoksikarbonil, karboksi, hidroksietil, 3-hidroksi-propenil, 2-amino-etil, metilurea, 2-morfolin-4-il-etil, (4-metil-piperazin-1-il)-etil, 2-dietilamino-etil, 2-(2-hidroksi-etilamino)-etil, propilaminoetil ili dietilamin.
14. Spoj prema bilo kojem od patentnih zahtjeva 1-13, naznačen time što ima opću formulu Ia.
15. Spoj prema bilo kojem od patentnih zahtjeva 1-13, naznačen time što ima opću formulu Ib.
16. Spoj prema bilo kojem od patentnih zahtjeva 1-13, naznačen time što je izabran iz grupe koju čine [2-Kloro-4-(2,4-difluorofenilamino)-fenil]-(2-metil-5-{1-[2-(tetrahidropiran-2-iloksi)-etil]-1H-[1,2,3] triazol-4-il}-fenil)-metanon (spoj 101), [2- Kloro-4-(2,4-difluoro-fenilamino)-fenil]-{5-[1-(2-hidroksi-etil)-1H-[1,2,3]triazol-4-il]-2-metil -fenil}-metanon (spoj 102), [2-Kloro-4-(2,4-difluoro-fenilamino)-fenil]-(2-metil-5-{1-[3-(tetrahidropiran-2-iloksi)-propil]-1H-[1,2,3]triazol-4-il}-fenil)-metanon (spoj 103), [2-Kloro-4-(2,4-difluoro-fenilamino)-fenil]-{5-[1-(3-hidroksi-propil)-1H-[1,2,3]triazol-4-il]-2-metil-fenil}-metanon (spoj 104), [2-Kloro-4-(2,4-difluoro-fenilamino)-fenil]-{5-[1-(2,2-dimetil-[1,3]dioksolan-4-ilmetil)-1H-[1,2,3]triazol-4-il]-2-metil-fenil}-metanon (spoj 105), [2-Kloro-4-(2,4-difluoro-fenilamino)-fenil]-{5-[1-(2,3-dihidroksi-propil)-1H-[1,2,3]triazol-4-il]-2-metil-fenil}-metanon (spoj 106), 2-(4-{3-[2-Kloro-4-(2,4-difluoro-fenilamino)-benzoil]-4-metil-fenil}-(1,2,3)triazol-1-il)-acetamid (spoj 107), Amid 3-(4-{3-[2-kloro-4-(2,4-difluoro-fenilamino)-benzoil]-4-metil-fenil}-[1,2,3]triazol-1-il)-propan-1-sulfonske kiseline (spoj 108), N-[2-(4-{3-[2-Kloro-4-(2,4-difluoro-fenilamino)-benzoil]-4-metil-fenil}-[1,2,3]triazol-1-il)-etil]-metansulfonamid (spoj 109), Etil ester (4-{3-[2-Kloro-4-(2,4-difluoro-fenilamino)-benzoil]-4-metil-fenil}-[1,2,3]triazol-1-il)-octene kiseline (spoj 110), (4-{3-[2-Kloro-4-(2,4-difluoro-fenilamino)-benzoil]-4-metil-fenil}-[1,2,3]triazol-1-il)-uctena kiselina (spoj 111), 2-(4-{3-[2-Kloro-4-(2,4-difluoro-fenilamino)-benzoil]-4-metil-fenil}-[1,2,3]triazol-1-il)-N-etil-acetamid (spoj 112), 2-(4-{3-[2-Kloro-4-(2,4-difluoro-fenilamino)-benzoil]-4-metil-fenil}-[1,2,3]triazol-1-il)-N-(2-hidroksi-1,1-dimetil-etil)-acetamid (spoj 113), 2-(4-{3-[2-Kloro-4-(2,4-difluoro-fenilamino)-benzoil]-4-metil-fenil}-[1,2,3]triazol-1-il)-1-pirolidin-1-il-etanon (spoj 114), 2-(4-{3-[2-Kloro-4-(2,4-difluoro-fenilamino)-benzoil]-4-metil-fenil}-[1,2,3]triazol-1-il)-1-morfolin-4-il-etanon (spoj 115), [2-Kloro-4-(4-trifluoro-metil-fenilamino)-fenil]-{5-[4-(2-hidroksi-etil)-[1,2,3]triazol-1-il]-2-metil-fenil}-metanon (spoj 116), (2-Kloro-4-o-tolilamino-fenil)-{5-[4-(2-hidroksi-etil)-[1,2,3]triazol-1-il]-2-metil-fenil}-metanon (spoj 117), [2-Kloro-4-(2-kloro-4-fluoro-fenilamino)-fenil]-{5-[4-(2-hidroksi-etil)-[1,2,3] triazol-1-il]-2-metil-fenil}-metanon (spoj 118), [2-Kloro-4-(2,4-difluoro-fenilamino)-fenil]-(2-metoksi-5-{1-[2-(tetrahidropiran-2-iloksi)-etil]-1H-[1,2,3] triazol-4-il}-fenil)-metanon (spoj 119), [2-Kloro-4-(2,4-difluoro-fenilamino)-fenil]-{5-[1-(2-hidroksi-etil)-1H-[1,2,3]triazol-4-il]-2-metoksi-fenil}-metanon (spoj 120), [2-Kloro-4-(4-fluoro-fenilamino)-fenil]-(2-metil-5-{1-[2-(tetrahidropiran-2-iloksi)-etil]-1H-[1,2,3]triazol-4-il}-fenil)-metanon (spoj 121), [2-Kloro-4-(4-fluoro-fenilamino)-fenil]-{5-[1-(2-hidroksi-etil)-1H-[1,2,3]triazol-4-il]-2-metil-fenil}-metanon (spoj 122), [2-Kloro-4-(4-fluoro-fenilamino)-fenil]-{5-[1-(2,2-dimetil-[1,3]dioksolan-4-ilmetil)-1H-[1,2,3] triazol-4-il]-2-metil-fenil}-metanon (spoj 123), [2-Kloro-4-(4-fluoro-fenilamino)-fenil]-{5-[1-(2,3-dihidroksi-propil)-1H-[1,2,3]triazol-4-il]-2-metil-fenil}-metanon (spoj 124), 2-(4-{3-[2-Kloro-4-(4-fluoro-fenilamino)-benzoil]-4-metil-fenil}-[1,2,3]triazol-1-il)-acetamid (spoj 125), [2-kloro-4-(2,4-difluoro-fenilamino)-fenil]-{5-[1-(2-kloro-etil)-1H-[1,2,3] triazol-4-il]-2-metil-fenil}-metanon (spoj 126) [2-Kloro-4-(4-fluoro-fenilamino)-fenil]-{5-[4-(2-hidroksi-etil)-[1,2,3]triazol-1-il]-2-metil-fenil}-metanon (spoj 127), [2-Kloro-4-(2,4-difluoro-fenilamino)-fenil]-{5-[4-(2-hidroksi-etil)-[1,2,3]triazol-1-il]-2-metil-fenil}-metanon (spoj 128), [2-Kloro-4-(2,4-difluoro-fenilamino)-fenil]-{5-[4-(1-hidroksi-1-metiletil)-[1,2,3]triazol-1-il]-2-metil-fenil}-metanon (spoj 129), 1-(1-{3-[2-Kloro-4-(2,4-difluoro-fenilamino)-benzoil]-4-metil-fenil}-1H-[1,2,3]triazol-4-il)-etanon (spoj 130), {5-[4-(1-Amino-1-metil-etil)-[1,2,3]triazol-1-il]-2-metil-fenil}-[2-kloro-4-(2,4-difluoro-fenilamino)-fenil]-metanon (spoj 131), Metil ester 1-{3-[2-kloro-4-(2,4-difluoro-fenilamino)-benzoil]-4-metil-fenil}-1H-[1,2,3]triazol-4-karbonske kiseline (spoj 132), 1-{3-[2-Kloro-4-(2,4-difluoro-fenilamino)-benzoil]-4-metil-fenil}1H-[1,2,3]triazol-4-karbonska kiselina (spoj 133), [2-Kloro-4-(2,4-difluoro-fenilamino)-fenil]-[5-(4-hidroksimetil-[1,2,3] triazol-1-il)-2-metil-fenil]-metanon (spoj 134), [2-Kloro-4-(2,4-difluoro-fenilamino)-fenil]-{5-[4-(3-hidroksi-propenil)-[1,2,3] triazol-1-il]-2-metil-fenil}-metanon (spoj 135), {5-[4-(2-Amino-etil)-[1,2,3]triazol-1-il]-2-metil-fenil}-[2-kloro-4-(2,4-difluoro-fenilamino)-fenil]-metanon (spoj 136), (1-{3-[2-Kloro-4-(2,4-difluoro-fenilamino)-benzoil]-4-metil-fenil}-1H-[1,2,3]triazol-4-ilmetil)-urea (spoj 137), [2-Kloro-4-(2,4-difluoro-fenilamino)-fenil]-{2-metil-5-[4-(2-morfolin-4-il-etil)-[1,2,3]triazol-1-il]-fenil}-metanon (spoj 138), [2-Kloro-4-(2,4-difluoro-fenilamino)-fenil]-(2-metil-5-{4-[2-(4-metil-piperazin-1-il)-etil]-[1,2,3]triazol-1-il}-fenil)-metanon (spoj 139), [2-Kloro-4-(2,4-difluoro-fenilamino)-fenil]-{5-[4-(2-dietilamino-etil)-[1,2,3]triazol-1-il]-2-metil-fenil}-metanon (spoj 140), [2-Kloro-4-(2,4-difluoro-fenilamino)-fenil]-(5-{4-[2-(2-hidroksi-etilamino)-etil]-[1,2,3]triazol-1-il}-2-metil-fenil)-metanon (spoj 141), [2-Kloro-4-(2,4-difluoro-fenilamino)-fenil]-{2-metil-5-[4-(2-propilaminoetil)-[1,2,3]triazol-1-il]-fenil}-metanon (spoj 142), [2-Kloro-4-(4-fluoro-2-metil-fenilamino)-fenil]-{5-[4-(2-hidroksietil)-[1,2,3]triazol-1-il]-2-metil-fenil}-metanon (spoj 143), [2-Kloro-4-(2-metoksi-fenilamino)-fenil]-{5-[4-(2-hidroksi-etil)-[1,2,3]triazol-1-il]-2-metil-fenil}-metanon (spoj 144), [2-Kloro-4-(4-kloro-2-metil-fenilamino)-fenil]-{5-[4-(2-hidroksi-etil)-[1,2,3]triazol-1-il]-2-metil-fenil}-metanon (spoj 145), [2-Kloro-4-(4-metoksi-fenilamino)-fenil]-{5-[4-(2-hidroksi-etil)-[1,2,3]triazol-1-il]-2-metil-fenil}-metanon (spoj 146), [2-Kloro-4-(2,4-difluoro-fenilamino)-fenil]-{5-[4-(2-etilamino-etil)-[1,2,3] triazol-1-il]-2-metil-fenil}-metanon (spoj 147), [4-(2,4-Difluoro-fenilamino)-2-metil-fenil]-{5-[4-(2-hidroksi-etil)-[1,2,3]triazol-1-il]-2-metil-fenil}-metanon (spoj 148), [4-(3-Kloro-4-fluoro-fenilamino)-2-metil-fenil]-{5-[4-(2-hidroksi-etil)-[1,2,3]triazol-1-il]-2-metil-fenil}-metanon (spoj 149), {5-[4-(2-Hidroksi-etil)-[1,2,3]triazol-1-il]-2-metil-fenil}-(2-metil-4-fenilamino-fenil)-metanon (spoj 150), 1-[3-(4-{5-[4-(2-Hidroksi-etil)-[1,2,3] triazol-1-il]-2-metil-benzoil}-3-metil-fenilamino)-fenil]-etanon (spoj 151), 3-(4-{5-[4-(2-Hidroksi-etil)-[1,2,3]triazol-1-il]-2-metil-benzoil}-3-metilfenilamino)-benzonitril (spoj 152), {5-[4-(2-Hidroksi-etil)-[1,2,3]triazol-1-il]-2-metil-fenil}-[2-metil-4-(3-trifluorometil-fenilamino)-fenil]-metanon (spoj 153), [4-(3,4-Difluoro-fenilamino)-2-metil-fenil]-{5-[4-(2-hidroksi-etil)-[1,2,3]triazol-1-il]-2-metil-fenil}-metanon (spoj 154), [4-(3,4-Dimetil-fenilamino)-2-metil-fenil]-{5-[4-(2-hidroksi-etil)-[1,2,3]triazol-1-il]-2-metil-fenil}-metanon (spoj 155), [4-(3-Kloro-2-metil-fenilamino)-2-metil-fenil]-{5-[4-(2-hidroksi-etil)-[1,2,3]triazol-1-il]-2-metil-fenil}-metanon (spoj 156), [4-(3,4-Dikloro-fenilamino)-2-metil-fenil]-{5-[4-(2-hidroksi-etil)-[1,2,3]triazol-1-il]-2-metil-fenil}-metanon (spoj 157), N-[3-(4-{5-[4-(2-Hidroksi-etil)-[1,2,3]triazol-1-il]-2-metil-benzoil}-3-metil-fenilamino)-fenil]-acetamid (spoj 158), [2-Kloro-4-(2,4-difluoro-fenilamino)-fenil]-{2-kloro-5-[4-(2-hidroksietil)-[1,2,3]triazol-1-il]-fenil}-metanon (spoj 159), [2-Kloro-4-(3-fluoro-fenilamino)-fenil]-{5-[4-(2-hidroksi-etil)-[1,2,3]triazol-1-il]-2-metil-fenil}-metanon (spoj 160), [2-Kloro-4-(3-kloro-fenilamino)-fenil]-{5-[4-(2-hidroksi-etil)-[1,2,3] triazol-1-il]-2-metil-fenil}-metanon (spoj 161), (2-Kloro-4-m-tolilamino-fenil)-{5-[4-(2-hidroksi-etil)-[1,2,3]triazol-1-il]-2-metil-fenil}-metanon (spoj 162), [2-Kloro-4-(3-metoksi-fenilamino)-fenil]-{5-[4-(2-hidroksi-etil)-[1,2,3]triazol-1-il]-2-metil-fenil}-metanon (spoj 163), [2-Kloro-4-(2,3-dikloro-fenilamino)-fenil]-{5-[4-(2-hidroksi-etil)-[1,2,3] triazol-1-il]-2-metil-fenil}-metanon (spoj 164), [2-Kloro-4-(3,5-dimetil-fenilamino)-fenil]-{5-[4-(2-hidroksi-etil)-[1,2,3]triazol-1-il]-2-metil-fenil}-metanon (spoj 165), [2-Kloro-4-(2,5-difluoro-fenilamino)-fenil]-{5-[4-(2-hidroksi-etil)-[1,2,3]triazol-1-il]-2-metil-fenil}-metanon (spoj 166) i [2-Kloro-4-(3,5-difluoro-fenilamino)-fenil]-{5-[4-(2-hidroksi-etil)-[1,2,3]triazol-1-il]-2-metil-fenil}-metanon (spoj 167).
17. Farmaceutska kompozicija, naznačena time što sadrži spoj prema bilo kojem od patentnih zahtjeva 1-16 ili njegovu farmaceutski prihvatljivu sol, zajedno sa farmaceutski prihvatljivim nosačem ili inertnim puniteljem.
18. Kompozicija prema patentnom zahtjevu 17, naznačena time što dalje sadrži drugu aktivnu komponentu izabranu iz grupe koju čine glukokortikoidi, analozi vitamina D, antihistaminici, antagonisti faktora aktivacije trombocita (PAF), antiholinergička sredstva, metil ksantini, β-adrenergička sredstva, inhibitori COX-2, salicilati, indometacin, flufenamat, naproksen, timegadin, soli zlata, peniciliamin, sredstva za snižavanje kolesterola u serumu, retinoidi, soli cinka i salicilazosulfapiridin.
19. Spoj prema bilo kojem od patentnih zahtjeva 1-16, naznačen time što se koristi za primjenu kao lijek.
20. Spoj prema bilo kojem od patentnih zahtjeva 1-16, naznačen time što se koristi za primjenu kao anti-inflamatorno sredstvo ili sredstvo protiv kancera.
21. Primjena spojeva prema bilo kojem od patentnih zahtjeva 1-16, naznačena time što se koristi za proizvodnju lijeka za profilaksu, liječenje ili poboljšanje inflamatornih bolesti ili stanja, ili oftalmičkih bolesti ili stanja.
22. Primjena spojeva prema bilo kojem od patentnih zahtjeva 1-16, naznačena time što se koristi za proizvodnju lijeka za liječenje ili poboljšanje kancera.
23. Primjena prema patentnom zahtjevu 21, naznačena time što je lijek namijenjen za primjenu zajedno sa drugom aktivnom komponentom koja je izabrana iz grupe koju čine glukokortikoidi, analozi vitamina D, antihistaminici, antagonisti faktora aktivacije trombocita (PAF), antiholinergička sredstva, metil ksantini, β-adrenergička sredstva, inhibitori COX-2, salicilati, indometacin, flufenamat, naproksen, timegadin, soli zlata, peniciliamin, sredstva za snižavanje kolesterola u serumu, retinoidi, soli cinka i salicilazosulfapiridin.
24. Primjena prema patentnom zahtjevu 21 ili 23, naznačena time što je inflamatorna bolest ili stanje astma, alergija, artritis, reumatoidni artritis, spondiloartritis, giht, ateroskleroza, kronična inflamatorna bolest crijeva, Crohn-ova bolest, neurološke inflamacije, inflamatorne bolesti oka, proliferativni i inflamatorni poremećaji kože, psorijaza, atopijski dermatitis, akne, uveitis, sepsa, septički šok ili osteoporoza.
25. Primjena prema patentnom zahtjevu 21, naznačena time što je oftalmička bolest akutna makularna degeneracija ili makularna degeneracija povezana sa starenjem.
26. Spoj prema bilo kojem od patentnih zahtjeva 1-16, naznačen time što se koristi za primjenu u liječenju, prevenciji ili poboljšanju inflamatornih bolesti ili stanja, kancera ili oftalmičkih bolesti ili stanja.
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MX2010006241A (es) * | 2007-12-18 | 2010-06-30 | Actelion Pharmaceuticals Ltd | Derivados de aminotriazol como agonistas de alx. |
ES2536794T3 (es) * | 2008-03-26 | 2015-05-28 | Chong Kun Dang Pharmaceutical Corp. | Derivados de benzofenona tiazol útiles para inhibir la formación de microtúbulos y método de producción de los mismos |
US8822513B2 (en) | 2010-03-01 | 2014-09-02 | Gtx, Inc. | Compounds for treatment of cancer |
US9029408B2 (en) | 2008-06-16 | 2015-05-12 | Gtx, Inc. | Compounds for treatment of cancer |
US9447049B2 (en) | 2010-03-01 | 2016-09-20 | University Of Tennessee Research Foundation | Compounds for treatment of cancer |
EP3289876B1 (en) | 2008-06-16 | 2022-07-20 | University of Tennessee Research Foundation | Compounds for treatment of cancer |
AU2010335654B2 (en) | 2009-12-22 | 2015-04-09 | Leo Pharma A/S | Cutaneous composition comprising vitamin D analogue and a mixture of solvent and surfactants |
CA2785253A1 (en) | 2009-12-22 | 2011-06-30 | Leo Pharma A/S | Calcipotriol monohydrate nanocrystals |
MX2012007225A (es) | 2009-12-22 | 2012-07-30 | Leo Pharma As | Composicion farmaceutica que comprende mezcla de solventes y derivado o analogo de vitamina d. |
AU2010347233B2 (en) | 2010-03-01 | 2015-06-18 | Oncternal Therapeutics, Inc. | Compounds for treatment of cancer |
US8912184B1 (en) | 2010-03-01 | 2014-12-16 | Alzheimer's Institute Of America, Inc. | Therapeutic and diagnostic methods |
KR101666759B1 (ko) * | 2015-08-06 | 2016-10-18 | 경북대학교 산학협력단 | 1-벤조피란메틸-1h-1,2,3-트리아졸 유도체 및 이의 용도 |
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GB9701453D0 (en) * | 1997-01-24 | 1997-03-12 | Leo Pharm Prod Ltd | Aminobenzophenones |
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EP1210325B1 (en) | 1999-07-16 | 2004-10-06 | Leo Pharma A/S | Aminobenzophenones as inhibitors of il-1beta and tnf-alpha |
WO2001005744A1 (en) | 1999-07-16 | 2001-01-25 | Leo Pharmaceutical Products Ltd. A/S (Løvens Kemiske Fabrik Produktionsaktieselskab) | Novel aminobenzophenones |
ATE277897T1 (de) | 1999-07-16 | 2004-10-15 | Leo Pharma As | Aminobenzophenone als inhibitoren von il-1beta und tnf-alpha |
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- 2005-11-28 RU RU2007126648/04A patent/RU2394818C2/ru not_active IP Right Cessation
- 2005-11-28 CN CN2005800480385A patent/CN101115728B/zh not_active Expired - Fee Related
- 2005-11-28 DE DE602005019093T patent/DE602005019093D1/de active Active
- 2005-11-28 EP EP05804019A patent/EP1828148B1/en active Active
- 2005-11-28 UA UAA200707890A patent/UA90698C2/ru unknown
- 2005-11-28 AU AU2005316034A patent/AU2005316034B2/en not_active Ceased
- 2005-11-28 ES ES05804019T patent/ES2341473T3/es active Active
- 2005-11-28 ZA ZA200704809A patent/ZA200704809B/xx unknown
- 2005-11-28 PL PL05804019T patent/PL1828148T3/pl unknown
- 2005-11-28 MX MX2007006739A patent/MX2007006739A/es active IP Right Grant
- 2005-11-28 BR BRPI0518993-4A patent/BRPI0518993A2/pt not_active IP Right Cessation
- 2005-11-28 JP JP2007545836A patent/JP5015005B2/ja not_active Expired - Fee Related
- 2005-11-28 CA CA002590479A patent/CA2590479A1/en not_active Abandoned
- 2005-11-28 AT AT05804019T patent/ATE455768T1/de active
- 2005-11-28 KR KR1020077015959A patent/KR101260236B1/ko not_active IP Right Cessation
- 2005-11-28 WO PCT/DK2005/000757 patent/WO2006063585A1/en active Application Filing
- 2005-11-28 PT PT05804019T patent/PT1828148E/pt unknown
- 2005-12-02 US US11/292,064 patent/US8293772B2/en not_active Expired - Fee Related
- 2005-12-12 AR ARP050105193A patent/AR051792A1/es not_active Application Discontinuation
-
2007
- 2007-05-29 IL IL183513A patent/IL183513A0/en unknown
- 2007-07-10 NO NO20073574A patent/NO20073574L/no not_active Application Discontinuation
-
2010
- 2010-04-19 HR HR20100225T patent/HRP20100225T1/hr unknown
Also Published As
Publication number | Publication date |
---|---|
PL1828148T3 (pl) | 2010-08-31 |
CN101115728A (zh) | 2008-01-30 |
MX2007006739A (es) | 2007-08-02 |
RU2394818C2 (ru) | 2010-07-20 |
US8293772B2 (en) | 2012-10-23 |
CA2590479A1 (en) | 2006-06-22 |
WO2006063585A1 (en) | 2006-06-22 |
KR20070095945A (ko) | 2007-10-01 |
IL183513A0 (en) | 2007-09-20 |
DK1828148T3 (da) | 2010-05-17 |
JP5015005B2 (ja) | 2012-08-29 |
AU2005316034B2 (en) | 2012-01-19 |
ZA200704809B (en) | 2008-08-27 |
ES2341473T3 (es) | 2010-06-21 |
EP1828148A1 (en) | 2007-09-05 |
US20060128766A1 (en) | 2006-06-15 |
RU2007126648A (ru) | 2009-01-20 |
PT1828148E (pt) | 2010-05-04 |
JP2008523115A (ja) | 2008-07-03 |
CN101115728B (zh) | 2012-12-19 |
BRPI0518993A2 (pt) | 2008-12-23 |
UA90698C2 (en) | 2010-05-25 |
NO20073574L (no) | 2007-07-10 |
KR101260236B1 (ko) | 2013-05-06 |
ATE455768T1 (de) | 2010-02-15 |
DE602005019093D1 (de) | 2010-03-11 |
AR051792A1 (es) | 2007-02-07 |
AU2005316034A1 (en) | 2006-06-22 |
EP1828148B1 (en) | 2010-01-20 |
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