AU768512B2 - Aminobenzophenones as inhibitors of IL-1beta and TNF-alpha - Google Patents
Aminobenzophenones as inhibitors of IL-1beta and TNF-alpha Download PDFInfo
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- AU768512B2 AU768512B2 AU58069/00A AU5806900A AU768512B2 AU 768512 B2 AU768512 B2 AU 768512B2 AU 58069/00 A AU58069/00 A AU 58069/00A AU 5806900 A AU5806900 A AU 5806900A AU 768512 B2 AU768512 B2 AU 768512B2
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- Prior art keywords
- phenyl
- alkyl
- compound
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- chloro
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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 5
- 239000003112 inhibitor Substances 0.000 title description 4
- 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 title 1
- 108060008682 Tumor Necrosis Factor Proteins 0.000 title 1
- 102000000852 Tumor Necrosis Factor-alpha Human genes 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 175
- -1 hydroxy, mercapto Chemical group 0.000 claims abstract description 87
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 64
- 125000001424 substituent group Chemical group 0.000 claims abstract description 52
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 44
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 25
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 25
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 24
- 150000002367 halogens Chemical group 0.000 claims abstract description 24
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 23
- 239000001257 hydrogen Substances 0.000 claims abstract description 23
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 23
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 21
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 17
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims abstract description 15
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims abstract description 12
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 12
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims abstract description 7
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 7
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 7
- 150000003839 salts Chemical class 0.000 claims abstract description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000001301 oxygen Substances 0.000 claims abstract description 6
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 6
- 239000012453 solvate Substances 0.000 claims abstract description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000005864 Sulphur Chemical group 0.000 claims abstract description 4
- 125000004429 atom Chemical group 0.000 claims abstract description 4
- 125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims abstract 10
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims abstract 10
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims abstract 10
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract 7
- 238000002560 therapeutic procedure Methods 0.000 claims abstract 2
- 238000000034 method Methods 0.000 claims description 66
- 241000894007 species Species 0.000 claims description 48
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 31
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 26
- 238000002360 preparation method Methods 0.000 claims description 26
- 239000004480 active ingredient Substances 0.000 claims description 24
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 24
- 238000011282 treatment Methods 0.000 claims description 23
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 22
- 125000003545 alkoxy group Chemical group 0.000 claims description 17
- 239000003795 chemical substances by application Substances 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 150000002431 hydrogen Chemical group 0.000 claims description 11
- 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 description 10
- 108010003541 Platelet Activating Factor Proteins 0.000 claims description 10
- 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 description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 125000003282 alkyl amino group Chemical group 0.000 claims description 9
- 239000003638 chemical reducing agent Substances 0.000 claims description 9
- 230000001684 chronic effect Effects 0.000 claims description 9
- 201000010099 disease Diseases 0.000 claims description 9
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 9
- 125000001153 fluoro group Chemical group F* 0.000 claims description 9
- KSAVQLQVUXSOCR-UHFFFAOYSA-M sodium lauroyl sarcosinate Chemical compound [Na+].CCCCCCCCCCCC(=O)N(C)CC([O-])=O KSAVQLQVUXSOCR-UHFFFAOYSA-M 0.000 claims description 9
- 230000002757 inflammatory effect Effects 0.000 claims description 8
- 206010012438 Dermatitis atopic Diseases 0.000 claims description 7
- 201000004681 Psoriasis Diseases 0.000 claims description 7
- 206010003246 arthritis Diseases 0.000 claims description 7
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- 201000008937 atopic dermatitis Diseases 0.000 claims description 7
- 208000030507 AIDS Diseases 0.000 claims description 6
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- 201000005569 Gout Diseases 0.000 claims description 6
- 206010020751 Hypersensitivity Diseases 0.000 claims description 6
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- 206010046851 Uveitis Diseases 0.000 claims description 6
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- 239000003937 drug carrier Substances 0.000 claims description 6
- 230000002062 proliferating effect Effects 0.000 claims description 6
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- 230000036303 septic shock Effects 0.000 claims description 6
- 210000002966 serum Anatomy 0.000 claims description 6
- 208000017520 skin disease Diseases 0.000 claims description 6
- 201000005671 spondyloarthropathy Diseases 0.000 claims description 6
- 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 description 5
- 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 description 5
- 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 description 5
- 208000002874 Acne Vulgaris Diseases 0.000 claims description 5
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 5
- 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 description 5
- 208000001132 Osteoporosis Diseases 0.000 claims description 5
- 229930003316 Vitamin D Natural products 0.000 claims description 5
- 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 description 5
- 206010000496 acne Diseases 0.000 claims description 5
- 239000000464 adrenergic agent Substances 0.000 claims description 5
- 239000005557 antagonist Substances 0.000 claims description 5
- 229940125715 antihistaminic agent Drugs 0.000 claims description 5
- 239000000739 antihistaminic agent Substances 0.000 claims description 5
- 229940067594 flufenamate Drugs 0.000 claims description 5
- 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 description 5
- 239000003862 glucocorticoid Substances 0.000 claims description 5
- 150000002343 gold Chemical class 0.000 claims description 5
- 229960000905 indomethacin Drugs 0.000 claims description 5
- 229960002009 naproxen Drugs 0.000 claims description 5
- 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 description 5
- 229960001639 penicillamine Drugs 0.000 claims description 5
- 150000003873 salicylate salts Chemical class 0.000 claims description 5
- 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 description 5
- 229940037128 systemic glucocorticoids Drugs 0.000 claims description 5
- 229950006828 timegadine Drugs 0.000 claims description 5
- 235000019166 vitamin D Nutrition 0.000 claims description 5
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- 150000003710 vitamin D derivatives Chemical class 0.000 claims description 5
- 229940046008 vitamin d Drugs 0.000 claims description 5
- 208000011231 Crohn disease Diseases 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- 230000001387 anti-histamine Effects 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 150000003751 zinc Chemical class 0.000 claims description 4
- YWXXLZKYWPWDLY-UHFFFAOYSA-N 4-[1-[[2-[3-chloro-4-(2-methylbenzoyl)anilino]phenyl]carbamoyloxy]ethoxy]-4-oxobutanoic acid Chemical compound OC(=O)CCC(=O)OC(C)OC(=O)NC1=CC=CC=C1NC(C=C1Cl)=CC=C1C(=O)C1=CC=CC=C1C YWXXLZKYWPWDLY-UHFFFAOYSA-N 0.000 claims description 3
- 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 3
- 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 3
- 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 3
- 150000007513 acids Chemical class 0.000 claims description 3
- 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 3
- 239000003814 drug Substances 0.000 claims description 3
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 150000004677 hydrates Chemical class 0.000 claims description 3
- JJSSWJLJQKHANC-UHFFFAOYSA-N 4-[[5-bromo-2-[3-chloro-4-(2-methylbenzoyl)anilino]phenyl]carbamoyloxymethoxy]-4-oxobutanoic acid Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=C(Br)C=C1NC(=O)OCOC(=O)CCC(O)=O JJSSWJLJQKHANC-UHFFFAOYSA-N 0.000 claims description 2
- 125000002837 carbocyclic group Chemical group 0.000 claims description 2
- AXEUOKPZHWOJJU-UHFFFAOYSA-N cyclopentyl n-[5-bromo-2-[3-chloro-4-(4-fluoro-2-methylbenzoyl)anilino]phenyl]carbamate Chemical compound CC1=CC(F)=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=C(Br)C=C1NC(=O)OC1CCCC1 AXEUOKPZHWOJJU-UHFFFAOYSA-N 0.000 claims description 2
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 2
- PUINBTOBPOTSJE-UHFFFAOYSA-N phenyl n-[2-[3-chloro-4-(2-methylbenzoyl)anilino]phenyl]carbamate Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1NC(=O)OC1=CC=CC=C1 PUINBTOBPOTSJE-UHFFFAOYSA-N 0.000 claims description 2
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims description 2
- 125000006592 (C2-C3) alkenyl group Chemical group 0.000 claims 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 125000006526 (C1-C2) alkyl group Chemical group 0.000 claims 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 1
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 1
- OWISYJXGRACROU-UHFFFAOYSA-N cyclohexyl n-[2-[3-chloro-4-(2-methylbenzoyl)anilino]phenyl]carbamate Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1NC(=O)OC1CCCCC1 OWISYJXGRACROU-UHFFFAOYSA-N 0.000 claims 1
- OQJOYEWUFIFWIT-UHFFFAOYSA-N cyclopentyl n-[2-[3-chloro-4-(2-methylbenzoyl)anilino]phenyl]carbamate Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1NC(=O)OC1CCCC1 OQJOYEWUFIFWIT-UHFFFAOYSA-N 0.000 claims 1
- XDTXOLHCZOWWPH-UHFFFAOYSA-N cyclopentyl n-[5-bromo-2-[3-chloro-4-(2,5-dimethylbenzoyl)anilino]phenyl]carbamate Chemical compound CC1=CC=C(C)C(C(=O)C=2C(=CC(NC=3C(=CC(Br)=CC=3)NC(=O)OC3CCCC3)=CC=2)Cl)=C1 XDTXOLHCZOWWPH-UHFFFAOYSA-N 0.000 claims 1
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 5
- 239000007858 starting material Substances 0.000 description 36
- 239000000203 mixture Substances 0.000 description 31
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 30
- 238000000746 purification Methods 0.000 description 26
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- 238000004587 chromatography analysis Methods 0.000 description 20
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 17
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- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 14
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- MSXZXFPYTVQJIL-UHFFFAOYSA-N [4-(2-aminoanilino)-2-chlorophenyl]-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1N MSXZXFPYTVQJIL-UHFFFAOYSA-N 0.000 description 10
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- 125000001246 bromo group Chemical group Br* 0.000 description 9
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 9
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- 238000005160 1H NMR spectroscopy Methods 0.000 description 8
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- NIAAGUPANRXQNB-UHFFFAOYSA-N 1-o-benzyl 4-o-[[2-[3-chloro-4-(2-methylbenzoyl)anilino]phenyl]carbamoyloxymethyl] butanedioate Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1NC(=O)OCOC(=O)CCC(=O)OCC1=CC=CC=C1 NIAAGUPANRXQNB-UHFFFAOYSA-N 0.000 description 5
- 102000004127 Cytokines Human genes 0.000 description 5
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- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 5
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- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
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- BPLUKJNHPBNVQL-UHFFFAOYSA-N triphenylarsine Chemical compound C1=CC=CC=C1[As](C=1C=CC=CC=1)C1=CC=CC=C1 BPLUKJNHPBNVQL-UHFFFAOYSA-N 0.000 description 1
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C07C271/58—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of six-membered aromatic rings with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/26—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring
- C07C271/28—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring to a carbon atom of a non-condensed six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/32—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C271/38—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of rings other than six-membered aromatic rings with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring
-
- 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
-
- 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
- C07C2601/14—The ring being saturated
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Physical Education & Sports Medicine (AREA)
- Rheumatology (AREA)
- Immunology (AREA)
- Epidemiology (AREA)
- Dermatology (AREA)
- Pulmonology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Pain & Pain Management (AREA)
- Virology (AREA)
- AIDS & HIV (AREA)
- Tropical Medicine & Parasitology (AREA)
- Heart & Thoracic Surgery (AREA)
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- Hematology (AREA)
- Ophthalmology & Optometry (AREA)
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- Urology & Nephrology (AREA)
- Oncology (AREA)
- Cardiology (AREA)
- Molecular Biology (AREA)
- Communicable Diseases (AREA)
- Emergency Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US14406399P | 1999-07-16 | 1999-07-16 | |
| US60/144063 | 1999-07-16 | ||
| PCT/DK2000/000386 WO2001005749A1 (en) | 1999-07-16 | 2000-07-11 | AMINOBENZOPHENONES AS INHIBITORS OF IL-1β AND TNF-$g(a) |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU5806900A AU5806900A (en) | 2001-02-05 |
| AU768512B2 true AU768512B2 (en) | 2003-12-18 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU58069/00A Ceased AU768512B2 (en) | 1999-07-16 | 2000-07-11 | Aminobenzophenones as inhibitors of IL-1beta and TNF-alpha |
Country Status (15)
| Country | Link |
|---|---|
| EP (1) | EP1202959B1 (https=) |
| JP (1) | JP2003505362A (https=) |
| KR (1) | KR20020022774A (https=) |
| CN (1) | CN1167667C (https=) |
| AT (1) | ATE277897T1 (https=) |
| AU (1) | AU768512B2 (https=) |
| CA (1) | CA2379286A1 (https=) |
| DE (1) | DE60014394T2 (https=) |
| ES (1) | ES2230118T3 (https=) |
| HU (1) | HUP0201911A3 (https=) |
| NZ (1) | NZ516825A (https=) |
| PL (1) | PL353646A1 (https=) |
| PT (1) | PT1202959E (https=) |
| RU (1) | RU2240995C2 (https=) |
| WO (1) | WO2001005749A1 (https=) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
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| HUP0301932A3 (en) | 2000-05-22 | 2007-09-28 | Leo Pharma As | Benzophenones as inhibitors of il-1 beta and tnf-alpha, pharmaceutical compositions containing them and use of them for producing pharmaceutical compositions |
| US8048917B2 (en) | 2005-04-06 | 2011-11-01 | Xenoport, Inc. | Prodrugs of GABA analogs, compositions and uses thereof |
| US6818787B2 (en) | 2001-06-11 | 2004-11-16 | Xenoport, Inc. | Prodrugs of GABA analogs, compositions and uses thereof |
| US7232924B2 (en) | 2001-06-11 | 2007-06-19 | Xenoport, Inc. | Methods for synthesis of acyloxyalkyl derivatives of GABA analogs |
| US7186855B2 (en) | 2001-06-11 | 2007-03-06 | Xenoport, Inc. | Prodrugs of GABA analogs, compositions and uses thereof |
| EP1423356A2 (en) * | 2001-08-28 | 2004-06-02 | Leo Pharma A/S | Novel aminobenzoephenones |
| US20030225089A1 (en) * | 2002-04-10 | 2003-12-04 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Pharmaceutical compositions based on anticholinergics and p38 kinase inhibitors |
| ES2278170T3 (es) | 2002-07-09 | 2007-08-01 | BOEHRINGER INGELHEIM PHARMA GMBH & CO.KG | Composiciones farmaceuticas de anticolinergicos e inhibidores de la quinasa p38 en el tratamiento de enfermedades respiratorias. |
| WO2004019873A2 (en) | 2002-08-29 | 2004-03-11 | Scios Inc. | Methods of promoting osteogenesis |
| CN1753861A (zh) * | 2002-12-20 | 2006-03-29 | 利奥制药有限公司 | 新颖的氨基二苯酮化合物 |
| DE602004027504D1 (de) * | 2003-07-24 | 2010-07-15 | Leo Pharma As | Aminobenzophenonverbindungen |
| WO2005030091A2 (en) | 2003-09-25 | 2005-04-07 | Scios Inc. | Stents and intra-luminal prostheses containing map kinase inhibitors |
| US20060035893A1 (en) | 2004-08-07 | 2006-02-16 | Boehringer Ingelheim International Gmbh | Pharmaceutical compositions for treatment of respiratory and gastrointestinal disorders |
| ES2341473T3 (es) | 2004-12-13 | 2010-06-21 | Leo Pharma A/S | Compuestos de aminobenzofenona sustituida con triazol. |
| PE20060777A1 (es) | 2004-12-24 | 2006-10-06 | Boehringer Ingelheim Int | Derivados de indolinona para el tratamiento o la prevencion de enfermedades fibroticas |
| EP1992344A1 (en) | 2007-05-18 | 2008-11-19 | Institut Curie | P38 alpha as a therapeutic target in pathologies linked to FGFR3 mutation |
| EP2315802A4 (en) * | 2008-07-31 | 2012-04-18 | 3M Innovative Properties Co | AZIUM COMPOSITIONS AND METHOD FOR THEIR PREPARATION AND USE |
| US8288005B2 (en) | 2008-07-31 | 2012-10-16 | 3M Innovative Properties Company | Fluoropolymer compositions and method of making and using thereof |
| EP2206534A1 (de) | 2008-10-09 | 2010-07-14 | c-a-i-r biosciences GmbH | Dibenzocycloheptanonderivate und pharmazeutische Mittel, welche diese Verbindungen enthalten |
Citations (1)
| 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 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1535401A (en) * | 1977-07-28 | 1978-12-13 | Holliday & Co Ltd L | Nitrodiphenylamine carboxylic acid disperse dyes |
| JPH0776303B2 (ja) * | 1986-11-21 | 1995-08-16 | 株式会社リコー | 呈色性フタリド化合物及びその製造法及びこのものを発色成分とした記録材料 |
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2000
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- 2000-07-11 ES ES00943700T patent/ES2230118T3/es not_active Expired - Lifetime
- 2000-07-11 DE DE60014394T patent/DE60014394T2/de not_active Expired - Fee Related
- 2000-07-11 CN CNB008121516A patent/CN1167667C/zh not_active Expired - Fee Related
- 2000-07-11 AT AT00943700T patent/ATE277897T1/de not_active IP Right Cessation
Patent Citations (1)
| 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 |
Also Published As
| Publication number | Publication date |
|---|---|
| DE60014394T2 (de) | 2005-12-22 |
| HUP0201911A2 (en) | 2002-10-28 |
| PT1202959E (pt) | 2005-01-31 |
| ATE277897T1 (de) | 2004-10-15 |
| HUP0201911A3 (en) | 2002-11-28 |
| KR20020022774A (ko) | 2002-03-27 |
| EP1202959A1 (en) | 2002-05-08 |
| JP2003505362A (ja) | 2003-02-12 |
| PL353646A1 (en) | 2003-12-01 |
| EP1202959B1 (en) | 2004-09-29 |
| DE60014394D1 (de) | 2004-11-04 |
| CA2379286A1 (en) | 2001-01-25 |
| CN1167667C (zh) | 2004-09-22 |
| ES2230118T3 (es) | 2005-05-01 |
| WO2001005749A1 (en) | 2001-01-25 |
| RU2240995C2 (ru) | 2004-11-27 |
| NZ516825A (en) | 2004-05-28 |
| HK1048303A1 (zh) | 2003-03-28 |
| AU5806900A (en) | 2001-02-05 |
| CN1371359A (zh) | 2002-09-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FGA | Letters patent sealed or granted (standard patent) |