ES2223116T3 - Aminobenzofenonas como inhibidores de interleucina y tnf. - Google Patents
Aminobenzofenonas como inhibidores de interleucina y tnf.Info
- Publication number
- ES2223116T3 ES2223116T3 ES98900270T ES98900270T ES2223116T3 ES 2223116 T3 ES2223116 T3 ES 2223116T3 ES 98900270 T ES98900270 T ES 98900270T ES 98900270 T ES98900270 T ES 98900270T ES 2223116 T3 ES2223116 T3 ES 2223116T3
- Authority
- ES
- Spain
- Prior art keywords
- compound
- nmr
- aminophenylamino
- general procedure
- phenyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 239000003112 inhibitor Substances 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 301
- -1 AMINO Chemical class 0.000 claims abstract description 32
- 238000011282 treatment Methods 0.000 claims abstract description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 8
- 239000001257 hydrogen Substances 0.000 claims abstract description 8
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 6
- 150000002367 halogens Chemical class 0.000 claims abstract description 6
- 201000004681 Psoriasis Diseases 0.000 claims abstract description 5
- 208000006673 asthma Diseases 0.000 claims abstract description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 4
- 230000002757 inflammatory effect Effects 0.000 claims abstract description 4
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 4
- 239000001301 oxygen Substances 0.000 claims abstract description 4
- 206010039073 rheumatoid arthritis Diseases 0.000 claims abstract description 4
- 201000001320 Atherosclerosis Diseases 0.000 claims abstract description 3
- 201000005569 Gout Diseases 0.000 claims abstract description 3
- 230000007815 allergy Effects 0.000 claims abstract description 3
- 230000002062 proliferating effect Effects 0.000 claims abstract description 3
- 201000005671 spondyloarthropathy Diseases 0.000 claims abstract description 3
- 239000003814 drug Substances 0.000 claims abstract 2
- 239000002253 acid Substances 0.000 claims description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 12
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 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 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 6
- 150000002431 hydrogen Chemical group 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- 125000003282 alkyl amino group Chemical group 0.000 claims description 4
- 125000004414 alkyl thio group Chemical group 0.000 claims description 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
- 125000004122 cyclic group Chemical group 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 4
- CNCCIXVSTNKJNB-UHFFFAOYSA-N 1-[2-(4-benzoylanilino)phenyl]-3-propylurea Chemical compound CCCNC(=O)NC1=CC=CC=C1NC1=CC=C(C(=O)C=2C=CC=CC=2)C=C1 CNCCIXVSTNKJNB-UHFFFAOYSA-N 0.000 claims description 3
- 206010012438 Dermatitis atopic Diseases 0.000 claims description 3
- BWNBZGHUSFIPPF-UHFFFAOYSA-N [4-(2-aminoanilino)-2-chlorophenyl]-(2,6-dimethylphenyl)methanone Chemical compound CC1=CC=CC(C)=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1N BWNBZGHUSFIPPF-UHFFFAOYSA-N 0.000 claims description 3
- RZMXKJYAVMSCOU-UHFFFAOYSA-N [4-(2-aminoanilino)-2-methoxyphenyl]-(2-methylphenyl)methanone Chemical compound C=1C=C(C(=O)C=2C(=CC=CC=2)C)C(OC)=CC=1NC1=CC=CC=C1N RZMXKJYAVMSCOU-UHFFFAOYSA-N 0.000 claims description 3
- PKXPHBHIGIXLGC-UHFFFAOYSA-N [4-(2-aminoanilino)phenyl]-(4-phenylmethoxyphenyl)methanone Chemical compound NC1=CC=CC=C1NC1=CC=C(C(=O)C=2C=CC(OCC=3C=CC=CC=3)=CC=2)C=C1 PKXPHBHIGIXLGC-UHFFFAOYSA-N 0.000 claims description 3
- YBRFCGFHBWJQHP-UHFFFAOYSA-N [4-(2-aminoanilino)phenyl]-[2-(phenoxymethyl)phenyl]methanone Chemical compound NC1=CC=CC=C1NC1=CC=C(C(=O)C=2C(=CC=CC=2)COC=2C=CC=CC=2)C=C1 YBRFCGFHBWJQHP-UHFFFAOYSA-N 0.000 claims description 3
- 201000008937 atopic dermatitis Diseases 0.000 claims description 3
- 230000001684 chronic effect Effects 0.000 claims description 3
- BGGSPEBQBGRQQF-UHFFFAOYSA-N n-[2-(4-benzoylanilino)phenyl]ethanesulfonamide Chemical compound CCS(=O)(=O)NC1=CC=CC=C1NC1=CC=C(C(=O)C=2C=CC=CC=2)C=C1 BGGSPEBQBGRQQF-UHFFFAOYSA-N 0.000 claims description 3
- IUCHYNQLCQUEBG-UHFFFAOYSA-N n-[2-(4-benzoylanilino)phenyl]methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC=CC=C1NC1=CC=C(C(=O)C=2C=CC=CC=2)C=C1 IUCHYNQLCQUEBG-UHFFFAOYSA-N 0.000 claims description 3
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- LAVHQYRXHKYWTM-UHFFFAOYSA-N 1-[2-(4-benzoylanilino)phenyl]-3-phenylurea Chemical compound C=1C=CC=C(NC=2C=CC(=CC=2)C(=O)C=2C=CC=CC=2)C=1NC(=O)NC1=CC=CC=C1 LAVHQYRXHKYWTM-UHFFFAOYSA-N 0.000 claims description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 2
- 206010020751 Hypersensitivity Diseases 0.000 claims description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 2
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims description 2
- SRBYHMOZHJUQQB-UHFFFAOYSA-N [4-(2-aminoanilino)-2-chlorophenyl]-(4-fluoro-2-methylphenyl)methanone Chemical compound CC1=CC(F)=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1N SRBYHMOZHJUQQB-UHFFFAOYSA-N 0.000 claims description 2
- VRSHRKWRSBPEAE-UHFFFAOYSA-N [4-(2-aminoanilino)-2-chlorophenyl]-[2-(trifluoromethyl)phenyl]methanone Chemical compound NC1=CC=CC=C1NC(C=C1Cl)=CC=C1C(=O)C1=CC=CC=C1C(F)(F)F VRSHRKWRSBPEAE-UHFFFAOYSA-N 0.000 claims description 2
- WXJXPMUVXLOTQU-UHFFFAOYSA-N [4-(2-aminoanilino)phenyl]-(2,3-dihydro-1,4-benzodioxin-6-yl)methanone Chemical compound NC1=CC=CC=C1NC1=CC=C(C(=O)C=2C=C3OCCOC3=CC=2)C=C1 WXJXPMUVXLOTQU-UHFFFAOYSA-N 0.000 claims description 2
- 208000026935 allergic disease Diseases 0.000 claims description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 2
- 235000019253 formic acid Nutrition 0.000 claims description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 2
- 239000011976 maleic acid Substances 0.000 claims description 2
- 229940098779 methanesulfonic acid Drugs 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 2
- 238000011321 prophylaxis Methods 0.000 claims description 2
- 208000017520 skin disease Diseases 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 239000011975 tartaric acid Substances 0.000 claims description 2
- 235000002906 tartaric acid Nutrition 0.000 claims description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims 2
- MVALDVBMYCYENV-UHFFFAOYSA-N n-[2-[3-chloro-4-(2-methylbenzoyl)anilino]phenyl]-2,2,2-trifluoroacetamide Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1NC(=O)C(F)(F)F MVALDVBMYCYENV-UHFFFAOYSA-N 0.000 claims 2
- 231100000252 nontoxic Toxicity 0.000 claims 2
- 230000003000 nontoxic effect Effects 0.000 claims 2
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical group [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims 2
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 claims 1
- UHTPDUNRQLNYOF-UHFFFAOYSA-N 3-[2-[3-chloro-4-(2-methylbenzoyl)anilino]phenyl]-1,1-dimethylurea Chemical compound CN(C)C(=O)NC1=CC=CC=C1NC(C=C1Cl)=CC=C1C(=O)C1=CC=CC=C1C UHTPDUNRQLNYOF-UHFFFAOYSA-N 0.000 claims 1
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims 1
- 229910021626 Tin(II) chloride Inorganic materials 0.000 claims 1
- 239000012752 auxiliary agent Substances 0.000 claims 1
- 239000003638 chemical reducing agent Substances 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- MBGPOESHRVIAJA-UHFFFAOYSA-N n-[2-(4-benzoyl-n-(2,2,2-trifluoroacetyl)anilino)phenyl]-2,2,2-trifluoroacetamide Chemical compound FC(F)(F)C(=O)NC1=CC=CC=C1N(C(=O)C(F)(F)F)C1=CC=C(C(=O)C=2C=CC=CC=2)C=C1 MBGPOESHRVIAJA-UHFFFAOYSA-N 0.000 claims 1
- DCMOFLCNFHPEAC-UHFFFAOYSA-N n-[2-(4-benzoylanilino)phenyl]-1-phenylmethanesulfonamide Chemical compound C=1C=C(NC=2C(=CC=CC=2)NS(=O)(=O)CC=2C=CC=CC=2)C=CC=1C(=O)C1=CC=CC=C1 DCMOFLCNFHPEAC-UHFFFAOYSA-N 0.000 claims 1
- FULXFPQLEOVYOF-UHFFFAOYSA-N n-[2-(4-benzoylanilino)phenyl]benzenesulfonamide Chemical compound C=1C=C(NC=2C(=CC=CC=2)NS(=O)(=O)C=2C=CC=CC=2)C=CC=1C(=O)C1=CC=CC=C1 FULXFPQLEOVYOF-UHFFFAOYSA-N 0.000 claims 1
- KIWXQPKZHFFGQG-UHFFFAOYSA-N n-[4-(4-benzoylanilino)phenyl]methanesulfonamide Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1NC1=CC=C(C(=O)C=2C=CC=CC=2)C=C1 KIWXQPKZHFFGQG-UHFFFAOYSA-N 0.000 claims 1
- 229910017604 nitric acid Inorganic materials 0.000 claims 1
- 239000001119 stannous chloride Substances 0.000 claims 1
- 235000011150 stannous chloride Nutrition 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- 201000004624 Dermatitis Diseases 0.000 abstract description 4
- 230000009885 systemic effect Effects 0.000 abstract description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- PMATZTZNYRCHOR-CGLBZJNRSA-N Cyclosporin A Chemical compound CC[C@@H]1NC(=O)[C@H]([C@H](O)[C@H](C)C\C=C\C)N(C)C(=O)[C@H](C(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)N(C)C(=O)CN(C)C1=O PMATZTZNYRCHOR-CGLBZJNRSA-N 0.000 abstract 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical class O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 abstract 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 abstract 1
- 229940072885 atopica Drugs 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 230000001079 digestive effect Effects 0.000 abstract 1
- 229940124597 therapeutic agent Drugs 0.000 abstract 1
- 238000005481 NMR spectroscopy Methods 0.000 description 159
- 238000000034 method Methods 0.000 description 153
- 238000000746 purification Methods 0.000 description 116
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 101
- 238000004587 chromatography analysis Methods 0.000 description 80
- 239000003480 eluent Substances 0.000 description 79
- 238000002360 preparation method Methods 0.000 description 72
- FGNLEIGUMSBZQP-UHFFFAOYSA-N cadaverine dihydrochloride Chemical compound Cl.Cl.NCCCCCN FGNLEIGUMSBZQP-UHFFFAOYSA-N 0.000 description 67
- 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 66
- 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 63
- PWKNBLFSJAVFAB-UHFFFAOYSA-N 1-fluoro-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1F PWKNBLFSJAVFAB-UHFFFAOYSA-N 0.000 description 49
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- 239000000203 mixture Substances 0.000 description 34
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 30
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- 238000002425 crystallisation Methods 0.000 description 23
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
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- 239000000243 solution Substances 0.000 description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
- 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 description 12
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- RAWYMBACZSQNDD-UHFFFAOYSA-N [4-(2-aminoanilino)phenyl]-phenylmethanone Chemical compound NC1=CC=CC=C1NC1=CC=C(C(=O)C=2C=CC=CC=2)C=C1 RAWYMBACZSQNDD-UHFFFAOYSA-N 0.000 description 12
- 239000013543 active substance Substances 0.000 description 11
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- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
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- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 8
- 210000004027 cell Anatomy 0.000 description 7
- 239000012074 organic phase Substances 0.000 description 7
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
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- 239000003795 chemical substances by application Substances 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- QSRRZKPKHJHIRB-UHFFFAOYSA-N methyl 4-[(2,5-dichloro-4-methylthiophen-3-yl)sulfonylamino]-2-hydroxybenzoate Chemical compound C1=C(O)C(C(=O)OC)=CC=C1NS(=O)(=O)C1=C(Cl)SC(Cl)=C1C QSRRZKPKHJHIRB-UHFFFAOYSA-N 0.000 description 6
- 238000001665 trituration Methods 0.000 description 6
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- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 5
- 102000000589 Interleukin-1 Human genes 0.000 description 5
- 108010002352 Interleukin-1 Proteins 0.000 description 5
- 229910052786 argon Inorganic materials 0.000 description 5
- 239000012965 benzophenone Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
- WFQDTOYDVUWQMS-UHFFFAOYSA-N 1-fluoro-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(F)C=C1 WFQDTOYDVUWQMS-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C225/00—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones
- C07C225/22—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Engineering & Computer Science (AREA)
- Dermatology (AREA)
- Rheumatology (AREA)
- Pulmonology (AREA)
- Urology & Nephrology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Pain & Pain Management (AREA)
- Immunology (AREA)
- Vascular Medicine (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB9701453 | 1997-01-24 | ||
| GBGB9701453.4A GB9701453D0 (en) | 1997-01-24 | 1997-01-24 | Aminobenzophenones |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2223116T3 true ES2223116T3 (es) | 2005-02-16 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES98900270T Expired - Lifetime ES2223116T3 (es) | 1997-01-24 | 1998-01-08 | Aminobenzofenonas como inhibidores de interleucina y tnf. |
Country Status (19)
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|---|---|
| US (1) | US6313174B1 (enExample) |
| EP (1) | EP0966424B1 (enExample) |
| JP (1) | JP4250204B2 (enExample) |
| KR (1) | KR100544046B1 (enExample) |
| CN (1) | CN1188388C (enExample) |
| AT (1) | ATE269844T1 (enExample) |
| AU (1) | AU733561B2 (enExample) |
| CA (1) | CA2278798C (enExample) |
| DE (1) | DE69824705T2 (enExample) |
| DK (1) | DK0966424T3 (enExample) |
| ES (1) | ES2223116T3 (enExample) |
| GB (1) | GB9701453D0 (enExample) |
| HU (1) | HUP0000678A3 (enExample) |
| NZ (1) | NZ336754A (enExample) |
| PL (1) | PL334806A1 (enExample) |
| PT (1) | PT966424E (enExample) |
| RO (1) | RO120195B1 (enExample) |
| RU (1) | RU2200153C2 (enExample) |
| WO (1) | WO1998032730A1 (enExample) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6750253B1 (en) | 1999-07-16 | 2004-06-15 | Leo Pharmaceutical Products Ltd. A/S | Aminobenzophenones as inhibitors of il-1β and tnf-α |
| NZ516824A (en) * | 1999-07-16 | 2004-03-26 | Leo Pharm Prod Ltd | Novel aminobenzophenones |
| US6897236B1 (en) | 1999-07-16 | 2005-05-24 | Leo Pharmaceutical Products, Ltd. | Aminobenzophenones as inhibitors of IL-1β and TNF-α |
| HUP0201846A3 (en) * | 1999-07-16 | 2002-11-28 | Leo Pharm Prod Ltd | Amonobenzophenones as inhibitors of il-1betha and tnf-alpha and pharmaceutical compositions containing them |
| DE60014394T2 (de) * | 1999-07-16 | 2005-12-22 | Leo Pharma A/S | Aminobenzophenone als inhibitoren von il-1beta und tnf-alpha |
| CA2379319A1 (en) * | 1999-07-16 | 2001-01-25 | Leo Pharmaceutical Products Ltd. A/S (Lovens Kemiske Fabrik Produktionsa Ktieselskab) | Aminobenzophenones as inhibitors of il-1.beta. and tnf-.alpha. |
| HUP0203813A3 (en) * | 1999-12-06 | 2008-03-28 | Leo Pharma As | Aminobenzophenones as inhibitors of il-1betha and tnf-alpha, pharmaceutical compositions containing them and their use |
| BR0012502A (pt) * | 1999-12-17 | 2003-06-24 | Abbott Lab | Inibidores da expressão do gene para interleucina 5 |
| AU2457201A (en) * | 1999-12-28 | 2001-07-09 | Bristol-Myers Squibb Company | Cytokine, especially tnf-alpha, inhibitors |
| CA2408727A1 (en) * | 2000-05-22 | 2001-11-29 | Leo Pharma A/S | Benzophenones as inhibitors of il-1.beta. and tnf-.alpha. |
| US20020165286A1 (en) * | 2000-12-08 | 2002-11-07 | Hanne Hedeman | Dermal anti-inflammatory composition |
| SE0100569D0 (sv) * | 2001-02-20 | 2001-02-20 | Astrazeneca Ab | New compounds |
| GB0107368D0 (en) * | 2001-03-23 | 2001-05-16 | Novartis Ag | Organic compounds |
| AU2002338286A1 (en) * | 2001-04-10 | 2002-10-28 | Leo Pharma A/S | Novel aminophenyl ketone derivatives |
| EP1423356A2 (en) * | 2001-08-28 | 2004-06-02 | Leo Pharma A/S | Novel aminobenzoephenones |
| BR0317445A (pt) * | 2002-12-20 | 2005-11-16 | Leo Pharma As | Composto, composição farmacêutica, método para o tratamento de doenças, e, uso de um composto |
| WO2005009940A1 (en) * | 2003-07-24 | 2005-02-03 | Leo Pharma A/S | Novel aminobenzophenone compounds |
| AU2005316034B2 (en) | 2004-12-13 | 2012-01-19 | Leo Pharma A/S | Triazole substituted aminobenzophenone compounds |
| DE102005022020A1 (de) * | 2005-05-12 | 2006-11-23 | Merckle Gmbh | Dibenzocycloheptanverbindungen und pharmazeutische Mittel, welche diese Verbindungen enthalten |
| KR101057546B1 (ko) * | 2007-06-05 | 2011-08-17 | 주식회사 엘지화학 | 광학 이방성 화합물 및 이를 포함하는 수지 조성물 |
| EP2206534A1 (de) | 2008-10-09 | 2010-07-14 | c-a-i-r biosciences GmbH | Dibenzocycloheptanonderivate und pharmazeutische Mittel, welche diese Verbindungen enthalten |
| WO2012167133A2 (en) * | 2011-06-01 | 2012-12-06 | The Regents Of The University Of California | Inhibitors of anandamide transport and their therapeutic uses |
| WO2013028570A2 (en) | 2011-08-19 | 2013-02-28 | The Regents Of The University Of California | Meta-substituted biphenyl peripherally restricted faah inhibitors |
| WO2015157313A1 (en) | 2014-04-07 | 2015-10-15 | The Regents Of The University Of California | Inhibitors of fatty acid amide hydrolase (faah) enzyme with improved oral bioavailability and their use as medicaments |
Family Cites Families (3)
| 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 |
| SU790620A1 (ru) * | 1979-06-01 | 1981-07-30 | Ордена Трудового Красного Знамени Институт Медицинскойпаразитологии И Торпической Медицины Им.E.И.Марциновского | Дихлор аминобензофенон как исходный продуктдл пОлучЕНи лЕКАРСТВЕННыХ пРЕпАРАТОВ C АНТигЕльМиНТНыМдЕйСТВиЕМ |
| 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 |
-
1997
- 1997-01-24 GB GBGB9701453.4A patent/GB9701453D0/en active Pending
-
1998
- 1998-01-08 US US09/341,923 patent/US6313174B1/en not_active Expired - Fee Related
- 1998-01-08 RO RO99-00839A patent/RO120195B1/ro unknown
- 1998-01-08 KR KR1019997006672A patent/KR100544046B1/ko not_active Expired - Fee Related
- 1998-01-08 EP EP98900270A patent/EP0966424B1/en not_active Expired - Lifetime
- 1998-01-08 AT AT98900270T patent/ATE269844T1/de active
- 1998-01-08 DE DE69824705T patent/DE69824705T2/de not_active Expired - Lifetime
- 1998-01-08 NZ NZ336754A patent/NZ336754A/xx not_active IP Right Cessation
- 1998-01-08 CN CNB988028301A patent/CN1188388C/zh not_active Expired - Fee Related
- 1998-01-08 PT PT98900270T patent/PT966424E/pt unknown
- 1998-01-08 HU HU0000678A patent/HUP0000678A3/hu unknown
- 1998-01-08 WO PCT/DK1998/000008 patent/WO1998032730A1/en not_active Ceased
- 1998-01-08 AU AU54781/98A patent/AU733561B2/en not_active Ceased
- 1998-01-08 ES ES98900270T patent/ES2223116T3/es not_active Expired - Lifetime
- 1998-01-08 JP JP53149998A patent/JP4250204B2/ja not_active Expired - Fee Related
- 1998-01-08 PL PL98334806A patent/PL334806A1/xx not_active IP Right Cessation
- 1998-01-08 DK DK98900270T patent/DK0966424T3/da active
- 1998-01-08 RU RU99118221/04A patent/RU2200153C2/ru not_active IP Right Cessation
- 1998-01-08 CA CA002278798A patent/CA2278798C/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| KR20000070437A (ko) | 2000-11-25 |
| KR100544046B1 (ko) | 2006-01-23 |
| EP0966424B1 (en) | 2004-06-23 |
| RU2200153C2 (ru) | 2003-03-10 |
| JP2001511771A (ja) | 2001-08-14 |
| NZ336754A (en) | 2001-03-30 |
| HUP0000678A2 (hu) | 2001-10-28 |
| GB9701453D0 (en) | 1997-03-12 |
| DK0966424T3 (da) | 2004-11-01 |
| RO120195B1 (ro) | 2005-10-28 |
| PL334806A1 (en) | 2000-03-13 |
| PT966424E (pt) | 2004-09-30 |
| ATE269844T1 (de) | 2004-07-15 |
| HK1025306A1 (en) | 2000-11-10 |
| DE69824705T2 (de) | 2005-07-07 |
| JP4250204B2 (ja) | 2009-04-08 |
| AU5478198A (en) | 1998-08-18 |
| EP0966424A1 (en) | 1999-12-29 |
| CA2278798C (en) | 2007-07-03 |
| CN1188388C (zh) | 2005-02-09 |
| AU733561B2 (en) | 2001-05-17 |
| WO1998032730A1 (en) | 1998-07-30 |
| US6313174B1 (en) | 2001-11-06 |
| HUP0000678A3 (en) | 2001-11-28 |
| CA2278798A1 (en) | 1998-07-30 |
| DE69824705D1 (de) | 2004-07-29 |
| CN1248966A (zh) | 2000-03-29 |
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