RU2200153C2 - Аминобензофеноны, способ их получения, фармацевтический препарат, способ лечения и профилактики воспалительных заболеваний кожи - Google Patents
Аминобензофеноны, способ их получения, фармацевтический препарат, способ лечения и профилактики воспалительных заболеваний кожи Download PDFInfo
- Publication number
- RU2200153C2 RU2200153C2 RU99118221/04A RU99118221A RU2200153C2 RU 2200153 C2 RU2200153 C2 RU 2200153C2 RU 99118221/04 A RU99118221/04 A RU 99118221/04A RU 99118221 A RU99118221 A RU 99118221A RU 2200153 C2 RU2200153 C2 RU 2200153C2
- Authority
- RU
- Russia
- Prior art keywords
- aminophenylamino
- compound
- benzophenone
- nmr
- amino
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 160
- 238000011282 treatment Methods 0.000 title claims abstract description 16
- MAOBFOXLCJIFLV-UHFFFAOYSA-N (2-aminophenyl)-phenylmethanone Chemical class NC1=CC=CC=C1C(=O)C1=CC=CC=C1 MAOBFOXLCJIFLV-UHFFFAOYSA-N 0.000 title claims abstract description 6
- 239000000825 pharmaceutical preparation Substances 0.000 title claims abstract description 4
- 230000015572 biosynthetic process Effects 0.000 title abstract description 5
- 238000003786 synthesis reaction Methods 0.000 title abstract description 5
- 208000027866 inflammatory disease Diseases 0.000 title abstract 3
- 238000011321 prophylaxis Methods 0.000 title abstract 3
- -1 alkylphenyl-sulfonyl Chemical group 0.000 claims abstract description 39
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 9
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 9
- 239000001257 hydrogen Substances 0.000 claims abstract description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 7
- 150000003839 salts Chemical class 0.000 claims abstract description 6
- 201000004681 Psoriasis Diseases 0.000 claims abstract description 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 5
- 206010012434 Dermatitis allergic Diseases 0.000 claims abstract description 4
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 4
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract description 4
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 4
- 201000008937 atopic dermatitis Diseases 0.000 claims abstract description 4
- 208000010668 atopic eczema Diseases 0.000 claims abstract description 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 4
- 239000003814 drug Substances 0.000 claims abstract description 3
- 231100000252 nontoxic Toxicity 0.000 claims abstract description 3
- 230000003000 nontoxic effect Effects 0.000 claims abstract description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 4
- 239000002253 acid Substances 0.000 claims abstract 2
- 150000007513 acids Chemical class 0.000 claims abstract 2
- 125000003342 alkenyl group Chemical group 0.000 claims abstract 2
- 125000003302 alkenyloxy group Chemical group 0.000 claims abstract 2
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims abstract 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims abstract 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims abstract 2
- 125000002071 phenylalkoxy group Chemical group 0.000 claims abstract 2
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims abstract 2
- 150000001875 compounds Chemical class 0.000 claims description 229
- 239000004480 active ingredient Substances 0.000 claims description 17
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 16
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 12
- 108060008682 Tumor Necrosis Factor Proteins 0.000 claims description 8
- 102000000852 Tumor Necrosis Factor-alpha Human genes 0.000 claims description 8
- 125000004429 atom Chemical group 0.000 claims description 8
- MZOFCQQQCNRIBI-VMXHOPILSA-N (3s)-4-[[(2s)-1-[[(2s)-1-[[(1s)-1-carboxy-2-hydroxyethyl]amino]-4-methyl-1-oxopentan-2-yl]amino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-3-[[2-[[(2s)-2,6-diaminohexanoyl]amino]acetyl]amino]-4-oxobutanoic acid Chemical compound OC[C@@H](C(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CC(O)=O)NC(=O)CNC(=O)[C@@H](N)CCCCN MZOFCQQQCNRIBI-VMXHOPILSA-N 0.000 claims 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
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 201000004624 Dermatitis Diseases 0.000 claims description 5
- 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
- 235000011054 acetic acid Nutrition 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical group 0.000 claims description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 4
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims description 4
- 230000028327 secretion Effects 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
- LHCRNWZLVYDHFQ-UHFFFAOYSA-N [4-(2-aminoanilino)phenyl]-(4-pentan-2-yloxyphenyl)methanone Chemical compound C1=CC(OC(C)CCC)=CC=C1C(=O)C(C=C1)=CC=C1NC1=CC=CC=C1N LHCRNWZLVYDHFQ-UHFFFAOYSA-N 0.000 claims description 3
- 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 description 3
- 230000002265 prevention Effects 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 235000019260 propionic acid Nutrition 0.000 claims description 3
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- LOGFVTREOLYCPF-KXNHARMFSA-N (2s,3r)-2-[[(2r)-1-[(2s)-2,6-diaminohexanoyl]pyrrolidine-2-carbonyl]amino]-3-hydroxybutanoic acid Chemical compound C[C@@H](O)[C@@H](C(O)=O)NC(=O)[C@H]1CCCN1C(=O)[C@@H](N)CCCCN LOGFVTREOLYCPF-KXNHARMFSA-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
- 102000003777 Interleukin-1 beta Human genes 0.000 claims description 2
- 108090000193 Interleukin-1 beta Proteins 0.000 claims description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 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
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 claims description 2
- 239000012965 benzophenone Substances 0.000 claims description 2
- 235000015165 citric acid Nutrition 0.000 claims description 2
- 201000010099 disease Diseases 0.000 claims description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 2
- 235000019253 formic acid Nutrition 0.000 claims description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 2
- 239000003112 inhibitor Substances 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
- 229910017604 nitric acid Inorganic materials 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 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
- 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 2
- 229910021626 Tin(II) chloride Inorganic materials 0.000 claims 1
- 239000000654 additive Substances 0.000 claims 1
- 239000003638 chemical reducing agent Substances 0.000 claims 1
- 238000011970 concomitant therapy Methods 0.000 claims 1
- ZHNUHDYFZUAESO-UHFFFAOYSA-N formamide Substances NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims 1
- 235000011150 stannous chloride Nutrition 0.000 claims 1
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 7
- 230000000694 effects Effects 0.000 abstract description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 3
- 239000000126 substance Substances 0.000 abstract description 3
- 125000004432 carbon atom Chemical group C* 0.000 abstract 4
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 2
- 125000005843 halogen group Chemical group 0.000 abstract 2
- 125000003277 amino group Chemical group 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 230000007721 medicinal effect Effects 0.000 abstract 1
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 259
- 239000007858 starting material Substances 0.000 description 204
- 238000000746 purification Methods 0.000 description 120
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 104
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 87
- 238000004587 chromatography analysis Methods 0.000 description 80
- 239000003480 eluent Substances 0.000 description 79
- 238000005160 1H NMR spectroscopy Methods 0.000 description 68
- FGNLEIGUMSBZQP-UHFFFAOYSA-N cadaverine dihydrochloride Chemical compound Cl.Cl.NCCCCCN FGNLEIGUMSBZQP-UHFFFAOYSA-N 0.000 description 68
- 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 50
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
- 239000000203 mixture Substances 0.000 description 34
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 28
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 27
- 238000002425 crystallisation Methods 0.000 description 24
- 230000008025 crystallization Effects 0.000 description 24
- 239000011541 reaction mixture Substances 0.000 description 23
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 239000000243 solution Substances 0.000 description 21
- 239000012043 crude product Substances 0.000 description 14
- 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
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- 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 11
- RBKHNGHPZZZJCI-UHFFFAOYSA-N (4-aminophenyl)-phenylmethanone Chemical compound C1=CC(N)=CC=C1C(=O)C1=CC=CC=C1 RBKHNGHPZZZJCI-UHFFFAOYSA-N 0.000 description 10
- 238000009472 formulation Methods 0.000 description 9
- 239000012074 organic phase Substances 0.000 description 9
- 239000002244 precipitate Substances 0.000 description 9
- 238000001665 trituration Methods 0.000 description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 7
- IMNFDUFMRHMDMM-UHFFFAOYSA-N anhydrous n-heptane Natural products CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 210000004027 cell Anatomy 0.000 description 6
- 238000003818 flash chromatography Methods 0.000 description 6
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 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
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- WFQDTOYDVUWQMS-UHFFFAOYSA-N 1-fluoro-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(F)C=C1 WFQDTOYDVUWQMS-UHFFFAOYSA-N 0.000 description 5
- 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 5
- 239000004615 ingredient Substances 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- ZVBQLJXNCHZULP-UHFFFAOYSA-N [2-methoxy-4-(2-nitroanilino)phenyl]-(2-methylphenyl)methanone Chemical compound C=1C=C(C(=O)C=2C(=CC=CC=2)C)C(OC)=CC=1NC1=CC=CC=C1[N+]([O-])=O ZVBQLJXNCHZULP-UHFFFAOYSA-N 0.000 description 4
- NSRUNIBQPCGWQC-UHFFFAOYSA-N [4-(2-nitroanilino)phenyl]-phenylmethanone Chemical compound [O-][N+](=O)C1=CC=CC=C1NC1=CC=C(C(=O)C=2C=CC=CC=2)C=C1 NSRUNIBQPCGWQC-UHFFFAOYSA-N 0.000 description 4
- 239000002552 dosage form Substances 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 230000004054 inflammatory process Effects 0.000 description 4
- 230000005764 inhibitory process Effects 0.000 description 4
- 239000002609 medium Substances 0.000 description 4
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 238000004809 thin layer chromatography Methods 0.000 description 4
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 4
- ZTOOEQPNJNCYIY-UHFFFAOYSA-N (2-methoxyphenyl)-[4-(2-nitroanilino)phenyl]methanone Chemical compound COC1=CC=CC=C1C(=O)C(C=C1)=CC=C1NC1=CC=CC=C1[N+]([O-])=O ZTOOEQPNJNCYIY-UHFFFAOYSA-N 0.000 description 3
- KWMMPYUINBQSLM-UHFFFAOYSA-N (4-amino-2-chlorophenyl)-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C1=CC=C(N)C=C1Cl KWMMPYUINBQSLM-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- MCTNFBIETWEFCK-UHFFFAOYSA-N [2-[(2-methylpropan-2-yl)oxy]phenyl]-[4-(2-nitroanilino)phenyl]methanone Chemical compound CC(C)(C)OC1=CC=CC=C1C(=O)C(C=C1)=CC=C1NC1=CC=CC=C1[N+]([O-])=O MCTNFBIETWEFCK-UHFFFAOYSA-N 0.000 description 3
- QYXJSCJLIYMOLO-UHFFFAOYSA-N [4-(3-aminoanilino)phenyl]-phenylmethanone Chemical compound NC1=CC=CC(NC=2C=CC(=CC=2)C(=O)C=2C=CC=CC=2)=C1 QYXJSCJLIYMOLO-UHFFFAOYSA-N 0.000 description 3
- HYWPRMOPWZFAML-UHFFFAOYSA-N [4-(4-aminoanilino)phenyl]-(2-hydroxyphenyl)methanone Chemical compound C1=CC(N)=CC=C1NC1=CC=C(C(=O)C=2C(=CC=CC=2)O)C=C1 HYWPRMOPWZFAML-UHFFFAOYSA-N 0.000 description 3
- BKHWZKJNNUUBHA-UHFFFAOYSA-N [4-[2-(methylamino)anilino]phenyl]-phenylmethanone Chemical compound CNC1=CC=CC=C1NC1=CC=C(C(=O)C=2C=CC=CC=2)C=C1 BKHWZKJNNUUBHA-UHFFFAOYSA-N 0.000 description 3
- 229910052786 argon Inorganic materials 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 239000002158 endotoxin Substances 0.000 description 3
- 229920006008 lipopolysaccharide Polymers 0.000 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 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- NKEZUMMUSHRNJQ-UHFFFAOYSA-N (2,3-dimethoxyphenyl)-[4-(2-nitroanilino)phenyl]methanone Chemical compound COC1=CC=CC(C(=O)C=2C=CC(NC=3C(=CC=CC=3)[N+]([O-])=O)=CC=2)=C1OC NKEZUMMUSHRNJQ-UHFFFAOYSA-N 0.000 description 2
- HROCTTHTWGSLIV-UHFFFAOYSA-N (2-bromophenyl)-[4-(2-nitroanilino)phenyl]methanone Chemical compound [O-][N+](=O)C1=CC=CC=C1NC1=CC=C(C(=O)C=2C(=CC=CC=2)Br)C=C1 HROCTTHTWGSLIV-UHFFFAOYSA-N 0.000 description 2
- ZZRKAXMYORBZLD-UHFFFAOYSA-N (2-chlorophenyl)-[4-(2-nitroanilino)phenyl]methanone Chemical compound [O-][N+](=O)C1=CC=CC=C1NC1=CC=C(C(=O)C=2C(=CC=CC=2)Cl)C=C1 ZZRKAXMYORBZLD-UHFFFAOYSA-N 0.000 description 2
- JAVDEZNTNSMASY-UHFFFAOYSA-N (2-ethylphenyl)-[4-(2-nitroanilino)phenyl]methanone Chemical compound CCC1=CC=CC=C1C(=O)C(C=C1)=CC=C1NC1=CC=CC=C1[N+]([O-])=O JAVDEZNTNSMASY-UHFFFAOYSA-N 0.000 description 2
- KGWASYNKFDVOJF-UHFFFAOYSA-N (2-hydroxyphenyl)-[4-(2-nitroanilino)phenyl]methanone Chemical compound OC1=CC=CC=C1C(=O)C(C=C1)=CC=C1NC1=CC=CC=C1[N+]([O-])=O KGWASYNKFDVOJF-UHFFFAOYSA-N 0.000 description 2
- DXEUMDIMBBHSGO-UHFFFAOYSA-N (2-hydroxyphenyl)-[4-(4-nitroanilino)phenyl]methanone Chemical compound OC1=CC=CC=C1C(=O)C(C=C1)=CC=C1NC1=CC=C([N+]([O-])=O)C=C1 DXEUMDIMBBHSGO-UHFFFAOYSA-N 0.000 description 2
- AZDWYCPAWIMJJY-UHFFFAOYSA-N (2-methylphenyl)-[4-(4-nitroanilino)phenyl]methanone Chemical compound CC1=CC=CC=C1C(=O)C(C=C1)=CC=C1NC1=CC=C([N+]([O-])=O)C=C1 AZDWYCPAWIMJJY-UHFFFAOYSA-N 0.000 description 2
- BGWIPQFBCJAOOY-UHFFFAOYSA-N (3,5-dichlorophenyl)-[4-(2-nitroanilino)phenyl]methanone Chemical compound [O-][N+](=O)C1=CC=CC=C1NC1=CC=C(C(=O)C=2C=C(Cl)C=C(Cl)C=2)C=C1 BGWIPQFBCJAOOY-UHFFFAOYSA-N 0.000 description 2
- YQWMPKMZLFHMCG-UHFFFAOYSA-N (3-butoxyphenyl)-[4-(2-nitroanilino)phenyl]methanone Chemical compound CCCCOC1=CC=CC(C(=O)C=2C=CC(NC=3C(=CC=CC=3)[N+]([O-])=O)=CC=2)=C1 YQWMPKMZLFHMCG-UHFFFAOYSA-N 0.000 description 2
- KQDWUIPQNXZQNI-UHFFFAOYSA-N (3-chlorophenyl)-[4-(2-nitroanilino)phenyl]methanone Chemical compound [O-][N+](=O)C1=CC=CC=C1NC1=CC=C(C(=O)C=2C=C(Cl)C=CC=2)C=C1 KQDWUIPQNXZQNI-UHFFFAOYSA-N 0.000 description 2
- CMORRFUJXQORPM-UHFFFAOYSA-N (3-fluorophenyl)-[4-(2-nitroanilino)phenyl]methanone Chemical compound [O-][N+](=O)C1=CC=CC=C1NC1=CC=C(C(=O)C=2C=C(F)C=CC=2)C=C1 CMORRFUJXQORPM-UHFFFAOYSA-N 0.000 description 2
- LKQJHLZCEYYWND-UHFFFAOYSA-N (3-methoxy-4-methylphenyl)-[4-(2-nitroanilino)phenyl]methanone Chemical compound C1=C(C)C(OC)=CC(C(=O)C=2C=CC(NC=3C(=CC=CC=3)[N+]([O-])=O)=CC=2)=C1 LKQJHLZCEYYWND-UHFFFAOYSA-N 0.000 description 2
- YUFCKWTYZVHHPS-UHFFFAOYSA-N (3-methylphenyl)-[4-(2-nitroanilino)phenyl]methanone Chemical compound CC1=CC=CC(C(=O)C=2C=CC(NC=3C(=CC=CC=3)[N+]([O-])=O)=CC=2)=C1 YUFCKWTYZVHHPS-UHFFFAOYSA-N 0.000 description 2
- MPVSFTZGKDYDIA-UHFFFAOYSA-N (4-aminophenyl)-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C1=CC=C(N)C=C1 MPVSFTZGKDYDIA-UHFFFAOYSA-N 0.000 description 2
- GEDXXHUDHPDFIB-UHFFFAOYSA-N (4-chloro-2-propan-2-ylsulfanylphenyl)-[4-(2-nitroanilino)phenyl]methanone Chemical compound CC(C)SC1=CC(Cl)=CC=C1C(=O)C(C=C1)=CC=C1NC1=CC=CC=C1[N+]([O-])=O GEDXXHUDHPDFIB-UHFFFAOYSA-N 0.000 description 2
- CHAFXDQBWVRNKJ-UHFFFAOYSA-N (4-chlorophenyl)-[4-(2-nitroanilino)phenyl]methanone Chemical compound [O-][N+](=O)C1=CC=CC=C1NC1=CC=C(C(=O)C=2C=CC(Cl)=CC=2)C=C1 CHAFXDQBWVRNKJ-UHFFFAOYSA-N 0.000 description 2
- PDZTULGOSOKXDH-UHFFFAOYSA-N (4-ethoxyphenyl)-[4-(2-nitroanilino)phenyl]methanone Chemical compound C1=CC(OCC)=CC=C1C(=O)C(C=C1)=CC=C1NC1=CC=CC=C1[N+]([O-])=O PDZTULGOSOKXDH-UHFFFAOYSA-N 0.000 description 2
- SKRYIRQSMYEHFD-UHFFFAOYSA-N (4-fluorophenyl)-[4-(2-nitroanilino)phenyl]methanone Chemical compound [O-][N+](=O)C1=CC=CC=C1NC1=CC=C(C(=O)C=2C=CC(F)=CC=2)C=C1 SKRYIRQSMYEHFD-UHFFFAOYSA-N 0.000 description 2
- FSLIBTBSEDSNJJ-UHFFFAOYSA-N (4-methoxyphenyl)-[4-(2-nitroanilino)phenyl]methanone Chemical compound C1=CC(OC)=CC=C1C(=O)C(C=C1)=CC=C1NC1=CC=CC=C1[N+]([O-])=O FSLIBTBSEDSNJJ-UHFFFAOYSA-N 0.000 description 2
- LOPOTOZBAGANAE-UHFFFAOYSA-N (4-tert-butylphenyl)-[4-(2-nitroanilino)phenyl]methanone Chemical compound C1=CC(C(C)(C)C)=CC=C1C(=O)C(C=C1)=CC=C1NC1=CC=CC=C1[N+]([O-])=O LOPOTOZBAGANAE-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- OORBDHOQLZRIQR-UHFFFAOYSA-N 1-fluoro-4-methyl-2-nitrobenzene Chemical compound CC1=CC=C(F)C([N+]([O-])=O)=C1 OORBDHOQLZRIQR-UHFFFAOYSA-N 0.000 description 2
- AWQFLWFGBRPFCK-UHFFFAOYSA-N 2,3-dihydro-1,4-benzodioxin-6-yl-[4-(2-nitroanilino)phenyl]methanone Chemical compound [O-][N+](=O)C1=CC=CC=C1NC1=CC=C(C(=O)C=2C=C3OCCOC3=CC=2)C=C1 AWQFLWFGBRPFCK-UHFFFAOYSA-N 0.000 description 2
- QSEHZVZOGZHGFA-UHFFFAOYSA-N 2-(4-benzoylanilino)-5-nitrobenzoic acid Chemical compound OC(=O)C1=CC([N+]([O-])=O)=CC=C1NC1=CC=C(C(=O)C=2C=CC=CC=2)C=C1 QSEHZVZOGZHGFA-UHFFFAOYSA-N 0.000 description 2
- PCPGELUNBJHCCD-UHFFFAOYSA-N 2-(4-benzoylanilino)-5-nitrobenzonitrile Chemical compound N#CC1=CC([N+](=O)[O-])=CC=C1NC1=CC=C(C(=O)C=2C=CC=CC=2)C=C1 PCPGELUNBJHCCD-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- RLIANWBWMDABQT-UHFFFAOYSA-N 3-[4-(2-aminoanilino)benzoyl]benzonitrile Chemical compound NC1=CC=CC=C1NC1=CC=C(C(=O)C=2C=C(C=CC=2)C#N)C=C1 RLIANWBWMDABQT-UHFFFAOYSA-N 0.000 description 2
- HHCOTKDIKFSJCV-UHFFFAOYSA-N 3-[4-(2-nitroanilino)benzoyl]benzonitrile Chemical compound [O-][N+](=O)C1=CC=CC=C1NC1=CC=C(C(=O)C=2C=C(C=CC=2)C#N)C=C1 HHCOTKDIKFSJCV-UHFFFAOYSA-N 0.000 description 2
- QJRDSGBCRYIKDM-UHFFFAOYSA-N 4-(4-benzoylanilino)-3-nitrobenzoic acid Chemical compound [O-][N+](=O)C1=CC(C(=O)O)=CC=C1NC1=CC=C(C(=O)C=2C=CC=CC=2)C=C1 QJRDSGBCRYIKDM-UHFFFAOYSA-N 0.000 description 2
- VFMTUFFQOGSCLW-UHFFFAOYSA-N 5-amino-2-(4-benzoylanilino)benzoic acid Chemical compound OC(=O)C1=CC(N)=CC=C1NC1=CC=C(C(=O)C=2C=CC=CC=2)C=C1 VFMTUFFQOGSCLW-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- 108010075031 Cytochromes c Proteins 0.000 description 2
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
- 206010061218 Inflammation Diseases 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 2
- 102000003896 Myeloperoxidases Human genes 0.000 description 2
- 108090000235 Myeloperoxidases Proteins 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- OIDINKBYMZMAFN-UHFFFAOYSA-N [2-chloro-4-(2-nitroanilino)phenyl]-(2,4,5-trifluorophenyl)methanone Chemical compound [O-][N+](=O)C1=CC=CC=C1NC(C=C1Cl)=CC=C1C(=O)C1=CC(F)=C(F)C=C1F OIDINKBYMZMAFN-UHFFFAOYSA-N 0.000 description 2
- ZRZPWOXLXVVHMI-UHFFFAOYSA-N [2-chloro-4-(2-nitroanilino)phenyl]-(2-methoxyphenyl)methanone Chemical compound COC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1[N+]([O-])=O ZRZPWOXLXVVHMI-UHFFFAOYSA-N 0.000 description 2
- WOUBHHLWOZLESX-UHFFFAOYSA-N [2-chloro-4-(2-nitroanilino)phenyl]-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1[N+]([O-])=O WOUBHHLWOZLESX-UHFFFAOYSA-N 0.000 description 2
- SOQWPUMUDMYPKV-UHFFFAOYSA-N [2-chloro-4-(2-nitroanilino)phenyl]-(4-chlorophenyl)methanone Chemical compound [O-][N+](=O)C1=CC=CC=C1NC(C=C1Cl)=CC=C1C(=O)C1=CC=C(Cl)C=C1 SOQWPUMUDMYPKV-UHFFFAOYSA-N 0.000 description 2
- VHWDIOGORGZUJR-UHFFFAOYSA-N [2-chloro-4-(2-nitroanilino)phenyl]-(4-fluoro-2-methylphenyl)methanone Chemical compound CC1=CC(F)=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1[N+]([O-])=O VHWDIOGORGZUJR-UHFFFAOYSA-N 0.000 description 2
- GIKAPSAHXQSGOR-UHFFFAOYSA-N [2-chloro-4-(2-nitroanilino)phenyl]-(4-methoxy-2,6-dimethylphenyl)methanone Chemical compound CC1=CC(OC)=CC(C)=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1[N+]([O-])=O GIKAPSAHXQSGOR-UHFFFAOYSA-N 0.000 description 2
- YMKUMJWHCQIANR-UHFFFAOYSA-N [2-chloro-4-(2-nitroanilino)phenyl]-[2-(trifluoromethyl)phenyl]methanone Chemical compound [O-][N+](=O)C1=CC=CC=C1NC(C=C1Cl)=CC=C1C(=O)C1=CC=CC=C1C(F)(F)F YMKUMJWHCQIANR-UHFFFAOYSA-N 0.000 description 2
- ZCBCMNJQWCIIRA-UHFFFAOYSA-N [2-chloro-4-(2-nitroanilino)phenyl]-phenylmethanone Chemical compound [O-][N+](=O)C1=CC=CC=C1NC(C=C1Cl)=CC=C1C(=O)C1=CC=CC=C1 ZCBCMNJQWCIIRA-UHFFFAOYSA-N 0.000 description 2
- BXULWPMIVOJNOX-UHFFFAOYSA-N [2-chloro-4-(4-nitroanilino)phenyl]-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=C([N+]([O-])=O)C=C1 BXULWPMIVOJNOX-UHFFFAOYSA-N 0.000 description 2
- XIRYWDBKGNTQNF-UHFFFAOYSA-N [3-(dimethylamino)phenyl]-[4-(2-nitroanilino)phenyl]methanone Chemical compound CN(C)C1=CC=CC(C(=O)C=2C=CC(NC=3C(=CC=CC=3)[N+]([O-])=O)=CC=2)=C1 XIRYWDBKGNTQNF-UHFFFAOYSA-N 0.000 description 2
- NZBKHKFXWYKROY-UHFFFAOYSA-N [3-amino-4-(4-aminoanilino)phenyl]-phenylmethanone Chemical compound C1=CC(N)=CC=C1NC1=CC=C(C(=O)C=2C=CC=CC=2)C=C1N NZBKHKFXWYKROY-UHFFFAOYSA-N 0.000 description 2
- YJGBHPGTCAWRTN-UHFFFAOYSA-N [3-methoxy-4-(2-nitroanilino)phenyl]-(2-methylphenyl)methanone Chemical compound COC1=CC(C(=O)C=2C(=CC=CC=2)C)=CC=C1NC1=CC=CC=C1[N+]([O-])=O YJGBHPGTCAWRTN-UHFFFAOYSA-N 0.000 description 2
- QGCWAKOGKAEBEQ-UHFFFAOYSA-N [3-methyl-4-(2-nitroanilino)phenyl]-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C(C=C1C)=CC=C1NC1=CC=CC=C1[N+]([O-])=O QGCWAKOGKAEBEQ-UHFFFAOYSA-N 0.000 description 2
- SZOABVJZOVLDNO-UHFFFAOYSA-N [3-methyl-4-(2-nitroanilino)phenyl]-phenylmethanone Chemical compound CC1=CC(C(=O)C=2C=CC=CC=2)=CC=C1NC1=CC=CC=C1[N+]([O-])=O SZOABVJZOVLDNO-UHFFFAOYSA-N 0.000 description 2
- QPKHCOAQQLJNEK-UHFFFAOYSA-N [3-nitro-4-(4-nitroanilino)phenyl]-phenylmethanone Chemical compound C1=CC([N+](=O)[O-])=CC=C1NC1=CC=C(C(=O)C=2C=CC=CC=2)C=C1[N+]([O-])=O QPKHCOAQQLJNEK-UHFFFAOYSA-N 0.000 description 2
- WYQSJSNNQFRLFU-UHFFFAOYSA-N [4-(2-amino-4-methylanilino)-2-chlorophenyl]-(2-methylphenyl)methanone Chemical compound NC1=CC(C)=CC=C1NC(C=C1Cl)=CC=C1C(=O)C1=CC=CC=C1C WYQSJSNNQFRLFU-UHFFFAOYSA-N 0.000 description 2
- IHKVEQDJFPKRNI-UHFFFAOYSA-N [4-(2-amino-4-methylanilino)phenyl]-phenylmethanone Chemical compound NC1=CC(C)=CC=C1NC1=CC=C(C(=O)C=2C=CC=CC=2)C=C1 IHKVEQDJFPKRNI-UHFFFAOYSA-N 0.000 description 2
- RNLACIIJGPESMP-UHFFFAOYSA-N [4-(2-amino-5-hydroxyanilino)phenyl]-phenylmethanone Chemical compound NC1=CC=C(O)C=C1NC1=CC=C(C(=O)C=2C=CC=CC=2)C=C1 RNLACIIJGPESMP-UHFFFAOYSA-N 0.000 description 2
- FTTXBLXGTRSINK-UHFFFAOYSA-N [4-(2-amino-n-methylanilino)phenyl]-phenylmethanone Chemical compound C=1C=CC=C(N)C=1N(C)C(C=C1)=CC=C1C(=O)C1=CC=CC=C1 FTTXBLXGTRSINK-UHFFFAOYSA-N 0.000 description 2
- UIFHFZAGDURXQR-UHFFFAOYSA-N [4-(2-aminoanilino)-2-chlorophenyl]-(2,4,5-trifluorophenyl)methanone Chemical compound NC1=CC=CC=C1NC(C=C1Cl)=CC=C1C(=O)C1=CC(F)=C(F)C=C1F UIFHFZAGDURXQR-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- AQXKGSIGOIIUJI-UHFFFAOYSA-N [4-(2-aminoanilino)-2-chlorophenyl]-(2-methoxyphenyl)methanone Chemical compound COC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1N AQXKGSIGOIIUJI-UHFFFAOYSA-N 0.000 description 2
- ZZPMSBPAIMHSNY-UHFFFAOYSA-N [4-(2-aminoanilino)-2-chlorophenyl]-(4-chlorophenyl)methanone Chemical compound NC1=CC=CC=C1NC(C=C1Cl)=CC=C1C(=O)C1=CC=C(Cl)C=C1 ZZPMSBPAIMHSNY-UHFFFAOYSA-N 0.000 description 2
- ITHPNVNBELRBSK-UHFFFAOYSA-N [4-(2-aminoanilino)-2-chlorophenyl]-phenylmethanone Chemical compound NC1=CC=CC=C1NC(C=C1Cl)=CC=C1C(=O)C1=CC=CC=C1 ITHPNVNBELRBSK-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- IDAPXKTVHNJIMG-UHFFFAOYSA-N [4-(2-aminoanilino)-3-chlorophenyl]-(4-methoxy-2,6-dimethylphenyl)methanone Chemical compound CC1=CC(OC)=CC(C)=C1C(=O)C(C=C1Cl)=CC=C1NC1=CC=CC=C1N IDAPXKTVHNJIMG-UHFFFAOYSA-N 0.000 description 2
- DVATTYQMAXXGKH-UHFFFAOYSA-N [4-(2-aminoanilino)-3-methoxyphenyl]-(2-methylphenyl)methanone Chemical compound COC1=CC(C(=O)C=2C(=CC=CC=2)C)=CC=C1NC1=CC=CC=C1N DVATTYQMAXXGKH-UHFFFAOYSA-N 0.000 description 2
- ZTCSEBJFMIAPGW-UHFFFAOYSA-N [4-(2-aminoanilino)-3-methylphenyl]-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C(C=C1C)=CC=C1NC1=CC=CC=C1N ZTCSEBJFMIAPGW-UHFFFAOYSA-N 0.000 description 2
- PMBPTWKJZOKGNA-UHFFFAOYSA-N [4-(2-aminoanilino)-3-methylphenyl]-phenylmethanone Chemical compound CC1=CC(C(=O)C=2C=CC=CC=2)=CC=C1NC1=CC=CC=C1N PMBPTWKJZOKGNA-UHFFFAOYSA-N 0.000 description 2
- PAZNPBLNNDGLOC-UHFFFAOYSA-N [4-(2-aminoanilino)phenyl]-(2,3,5,6-tetramethylphenyl)methanone Chemical compound CC1=CC(C)=C(C)C(C(=O)C=2C=CC(NC=3C(=CC=CC=3)N)=CC=2)=C1C PAZNPBLNNDGLOC-UHFFFAOYSA-N 0.000 description 2
- GRGSSXVLXSJQEX-UHFFFAOYSA-N [4-(2-aminoanilino)phenyl]-(2,3-dimethoxyphenyl)methanone Chemical compound COC1=CC=CC(C(=O)C=2C=CC(NC=3C(=CC=CC=3)N)=CC=2)=C1OC GRGSSXVLXSJQEX-UHFFFAOYSA-N 0.000 description 2
- YWUIYOLZZYLHHJ-UHFFFAOYSA-N [4-(2-aminoanilino)phenyl]-(2,4-dichlorophenyl)methanone Chemical compound NC1=CC=CC=C1NC1=CC=C(C(=O)C=2C(=CC(Cl)=CC=2)Cl)C=C1 YWUIYOLZZYLHHJ-UHFFFAOYSA-N 0.000 description 2
- MSGGRRJXKDUMOF-UHFFFAOYSA-N [4-(2-aminoanilino)phenyl]-(2-bromophenyl)methanone Chemical compound NC1=CC=CC=C1NC1=CC=C(C(=O)C=2C(=CC=CC=2)Br)C=C1 MSGGRRJXKDUMOF-UHFFFAOYSA-N 0.000 description 2
- FCHVFFKUWLDQRG-UHFFFAOYSA-N [4-(2-aminoanilino)phenyl]-(2-chlorophenyl)methanone Chemical compound NC1=CC=CC=C1NC1=CC=C(C(=O)C=2C(=CC=CC=2)Cl)C=C1 FCHVFFKUWLDQRG-UHFFFAOYSA-N 0.000 description 2
- RFUDCLSHRXNAGR-UHFFFAOYSA-N [4-(2-aminoanilino)phenyl]-(2-ethylphenyl)methanone Chemical compound CCC1=CC=CC=C1C(=O)C(C=C1)=CC=C1NC1=CC=CC=C1N RFUDCLSHRXNAGR-UHFFFAOYSA-N 0.000 description 2
- ANFIDPOYOSVCDZ-UHFFFAOYSA-N [4-(2-aminoanilino)phenyl]-(2-fluorophenyl)methanone Chemical compound NC1=CC=CC=C1NC1=CC=C(C(=O)C=2C(=CC=CC=2)F)C=C1 ANFIDPOYOSVCDZ-UHFFFAOYSA-N 0.000 description 2
- YCYKHGNTYJXARI-UHFFFAOYSA-N [4-(2-aminoanilino)phenyl]-(2-hydroxyphenyl)methanone Chemical compound NC1=CC=CC=C1NC1=CC=C(C(=O)C=2C(=CC=CC=2)O)C=C1 YCYKHGNTYJXARI-UHFFFAOYSA-N 0.000 description 2
- SIOLNXSDRQRYLQ-UHFFFAOYSA-N [4-(2-aminoanilino)phenyl]-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C(C=C1)=CC=C1NC1=CC=CC=C1N SIOLNXSDRQRYLQ-UHFFFAOYSA-N 0.000 description 2
- AWDLKMAFJRWGKY-UHFFFAOYSA-N [4-(2-aminoanilino)phenyl]-(2-phenylphenyl)methanone Chemical compound NC1=CC=CC=C1NC1=CC=C(C(=O)C=2C(=CC=CC=2)C=2C=CC=CC=2)C=C1 AWDLKMAFJRWGKY-UHFFFAOYSA-N 0.000 description 2
- CKDPZZGHRZCZDS-UHFFFAOYSA-N [4-(2-aminoanilino)phenyl]-(3,4,5-trimethoxyphenyl)methanone Chemical compound COC1=C(OC)C(OC)=CC(C(=O)C=2C=CC(NC=3C(=CC=CC=3)N)=CC=2)=C1 CKDPZZGHRZCZDS-UHFFFAOYSA-N 0.000 description 2
- QNBWVIFBTQPCQO-UHFFFAOYSA-N [4-(2-aminoanilino)phenyl]-(3,5-dichlorophenyl)methanone Chemical compound NC1=CC=CC=C1NC1=CC=C(C(=O)C=2C=C(Cl)C=C(Cl)C=2)C=C1 QNBWVIFBTQPCQO-UHFFFAOYSA-N 0.000 description 2
- PYHBFNSNYDVRJL-UHFFFAOYSA-N [4-(2-aminoanilino)phenyl]-(3-butoxyphenyl)methanone Chemical compound CCCCOC1=CC=CC(C(=O)C=2C=CC(NC=3C(=CC=CC=3)N)=CC=2)=C1 PYHBFNSNYDVRJL-UHFFFAOYSA-N 0.000 description 2
- GIHGGNYPUMSVDD-UHFFFAOYSA-N [4-(2-aminoanilino)phenyl]-(3-chlorophenyl)methanone Chemical compound NC1=CC=CC=C1NC1=CC=C(C(=O)C=2C=C(Cl)C=CC=2)C=C1 GIHGGNYPUMSVDD-UHFFFAOYSA-N 0.000 description 2
- WEFUVBRDWHTXGN-UHFFFAOYSA-N [4-(2-aminoanilino)phenyl]-(3-methoxy-4-methylphenyl)methanone Chemical compound C1=C(C)C(OC)=CC(C(=O)C=2C=CC(NC=3C(=CC=CC=3)N)=CC=2)=C1 WEFUVBRDWHTXGN-UHFFFAOYSA-N 0.000 description 2
- DGGKYCLSFAHSRL-UHFFFAOYSA-N [4-(2-aminoanilino)phenyl]-(3-phenylphenyl)methanone Chemical compound NC1=CC=CC=C1NC1=CC=C(C(=O)C=2C=C(C=CC=2)C=2C=CC=CC=2)C=C1 DGGKYCLSFAHSRL-UHFFFAOYSA-N 0.000 description 2
- IHPIZPGZOROZKN-UHFFFAOYSA-N [4-(2-aminoanilino)phenyl]-(4-chloro-2-propan-2-ylsulfanylphenyl)methanone Chemical compound CC(C)SC1=CC(Cl)=CC=C1C(=O)C(C=C1)=CC=C1NC1=CC=CC=C1N IHPIZPGZOROZKN-UHFFFAOYSA-N 0.000 description 2
- MLRZRDOKEZRUKD-UHFFFAOYSA-N [4-(2-aminoanilino)phenyl]-(4-chlorophenyl)methanone Chemical compound NC1=CC=CC=C1NC1=CC=C(C(=O)C=2C=CC(Cl)=CC=2)C=C1 MLRZRDOKEZRUKD-UHFFFAOYSA-N 0.000 description 2
- BQHFLGLUSZGXAL-UHFFFAOYSA-N [4-(2-aminoanilino)phenyl]-(4-ethoxyphenyl)methanone Chemical compound C1=CC(OCC)=CC=C1C(=O)C(C=C1)=CC=C1NC1=CC=CC=C1N BQHFLGLUSZGXAL-UHFFFAOYSA-N 0.000 description 2
- YARWYSREOYLETK-UHFFFAOYSA-N [4-(2-aminoanilino)phenyl]-(4-fluorophenyl)methanone Chemical compound NC1=CC=CC=C1NC1=CC=C(C(=O)C=2C=CC(F)=CC=2)C=C1 YARWYSREOYLETK-UHFFFAOYSA-N 0.000 description 2
- NKUZYUWILUZELN-UHFFFAOYSA-N [4-(2-aminoanilino)phenyl]-(4-pentylphenyl)methanone Chemical compound C1=CC(CCCCC)=CC=C1C(=O)C(C=C1)=CC=C1NC1=CC=CC=C1N NKUZYUWILUZELN-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- GJFAZZZBJGIULE-UHFFFAOYSA-N [4-(2-aminoanilino)phenyl]-(4-phenylphenyl)methanone Chemical compound NC1=CC=CC=C1NC1=CC=C(C(=O)C=2C=CC(=CC=2)C=2C=CC=CC=2)C=C1 GJFAZZZBJGIULE-UHFFFAOYSA-N 0.000 description 2
- BZGKWZDTCYCPCA-UHFFFAOYSA-N [4-(2-aminoanilino)phenyl]-(4-tert-butylphenyl)methanone Chemical compound C1=CC(C(C)(C)C)=CC=C1C(=O)C(C=C1)=CC=C1NC1=CC=CC=C1N BZGKWZDTCYCPCA-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- WUDPJKNXJHNPMA-UHFFFAOYSA-N [4-(2-aminoanilino)phenyl]-[2-[(2-methylpropan-2-yl)oxy]phenyl]methanone Chemical compound CC(C)(C)OC1=CC=CC=C1C(=O)C(C=C1)=CC=C1NC1=CC=CC=C1N WUDPJKNXJHNPMA-UHFFFAOYSA-N 0.000 description 2
- KWSVUVMYMJYSFJ-UHFFFAOYSA-N [4-(2-chloro-4-nitroanilino)phenyl]-phenylmethanone Chemical compound ClC1=CC([N+](=O)[O-])=CC=C1NC1=CC=C(C(=O)C=2C=CC=CC=2)C=C1 KWSVUVMYMJYSFJ-UHFFFAOYSA-N 0.000 description 2
- NPDYWHXQOIHOLN-UHFFFAOYSA-N [4-(2-methyl-4-nitroanilino)phenyl]-phenylmethanone Chemical compound CC1=CC([N+]([O-])=O)=CC=C1NC1=CC=C(C(=O)C=2C=CC=CC=2)C=C1 NPDYWHXQOIHOLN-UHFFFAOYSA-N 0.000 description 2
- FLYGTQADUBMPQQ-UHFFFAOYSA-N [4-(2-nitroanilino)phenyl]-(2,3,5,6-tetramethylphenyl)methanone Chemical compound CC1=CC(C)=C(C)C(C(=O)C=2C=CC(NC=3C(=CC=CC=3)[N+]([O-])=O)=CC=2)=C1C FLYGTQADUBMPQQ-UHFFFAOYSA-N 0.000 description 2
- MPZPFBJKVAKWCN-UHFFFAOYSA-N [4-(2-nitroanilino)phenyl]-(2-phenylphenyl)methanone Chemical compound [O-][N+](=O)C1=CC=CC=C1NC1=CC=C(C(=O)C=2C(=CC=CC=2)C=2C=CC=CC=2)C=C1 MPZPFBJKVAKWCN-UHFFFAOYSA-N 0.000 description 2
- NWTHOGJQTZENRP-UHFFFAOYSA-N [4-(2-nitroanilino)phenyl]-(3,4,5-trimethoxyphenyl)methanone Chemical compound COC1=C(OC)C(OC)=CC(C(=O)C=2C=CC(NC=3C(=CC=CC=3)[N+]([O-])=O)=CC=2)=C1 NWTHOGJQTZENRP-UHFFFAOYSA-N 0.000 description 2
- PDFBXNQMOCITBS-UHFFFAOYSA-N [4-(2-nitroanilino)phenyl]-(3-phenylphenyl)methanone Chemical compound [O-][N+](=O)C1=CC=CC=C1NC1=CC=C(C(=O)C=2C=C(C=CC=2)C=2C=CC=CC=2)C=C1 PDFBXNQMOCITBS-UHFFFAOYSA-N 0.000 description 2
- RKBABZHQQVKAJJ-UHFFFAOYSA-N [4-(2-nitroanilino)phenyl]-(4-pentylphenyl)methanone Chemical compound C1=CC(CCCCC)=CC=C1C(=O)C(C=C1)=CC=C1NC1=CC=CC=C1[N+]([O-])=O RKBABZHQQVKAJJ-UHFFFAOYSA-N 0.000 description 2
- XLWBPZPBKAVXSY-UHFFFAOYSA-N [4-(2-nitroanilino)phenyl]-(4-phenylmethoxyphenyl)methanone Chemical compound [O-][N+](=O)C1=CC=CC=C1NC1=CC=C(C(=O)C=2C=CC(OCC=3C=CC=CC=3)=CC=2)C=C1 XLWBPZPBKAVXSY-UHFFFAOYSA-N 0.000 description 2
- VHCFSVCHZMVNKC-UHFFFAOYSA-N [4-(2-nitroanilino)phenyl]-(4-phenylphenyl)methanone Chemical compound [O-][N+](=O)C1=CC=CC=C1NC1=CC=C(C(=O)C=2C=CC(=CC=2)C=2C=CC=CC=2)C=C1 VHCFSVCHZMVNKC-UHFFFAOYSA-N 0.000 description 2
- SOFYRFCSYNHSCW-UHFFFAOYSA-N [4-(2-nitroanilino)phenyl]-[2-(phenoxymethyl)phenyl]methanone Chemical compound [O-][N+](=O)C1=CC=CC=C1NC1=CC=C(C(=O)C=2C(=CC=CC=2)COC=2C=CC=CC=2)C=C1 SOFYRFCSYNHSCW-UHFFFAOYSA-N 0.000 description 2
- IEPWCQADZIVPKT-UHFFFAOYSA-N [4-(2-nitroanilino)phenyl]-[3-(trifluoromethyl)phenyl]methanone Chemical compound [O-][N+](=O)C1=CC=CC=C1NC1=CC=C(C(=O)C=2C=C(C=CC=2)C(F)(F)F)C=C1 IEPWCQADZIVPKT-UHFFFAOYSA-N 0.000 description 2
- MBEGTDUFPSTHIQ-UHFFFAOYSA-N [4-(2-nitroanilino)phenyl]-[4-(trifluoromethyl)phenyl]methanone Chemical compound [O-][N+](=O)C1=CC=CC=C1NC1=CC=C(C(=O)C=2C=CC(=CC=2)C(F)(F)F)C=C1 MBEGTDUFPSTHIQ-UHFFFAOYSA-N 0.000 description 2
- XIEQKSBJMIEYMR-UHFFFAOYSA-N [4-(3-nitroanilino)phenyl]-phenylmethanone Chemical compound [O-][N+](=O)C1=CC=CC(NC=2C=CC(=CC=2)C(=O)C=2C=CC=CC=2)=C1 XIEQKSBJMIEYMR-UHFFFAOYSA-N 0.000 description 2
- CXYPFXRWARMZHD-UHFFFAOYSA-N [4-(4-amino-2-methylanilino)phenyl]-phenylmethanone Chemical compound CC1=CC(N)=CC=C1NC1=CC=C(C(=O)C=2C=CC=CC=2)C=C1 CXYPFXRWARMZHD-UHFFFAOYSA-N 0.000 description 2
- VUJOLLZLDPCHRX-UHFFFAOYSA-N [4-(4-aminoanilino)-2-chlorophenyl]-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=C(N)C=C1 VUJOLLZLDPCHRX-UHFFFAOYSA-N 0.000 description 2
- PFDHJPHIZPCTSM-UHFFFAOYSA-N [4-(4-aminoanilino)phenyl]-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C(C=C1)=CC=C1NC1=CC=C(N)C=C1 PFDHJPHIZPCTSM-UHFFFAOYSA-N 0.000 description 2
- IXXZKRSKPJIKSU-UHFFFAOYSA-N [4-(4-aminoanilino)phenyl]-phenylmethanone Chemical compound C1=CC(N)=CC=C1NC1=CC=C(C(=O)C=2C=CC=CC=2)C=C1 IXXZKRSKPJIKSU-UHFFFAOYSA-N 0.000 description 2
- WPWNGERDPVIMSG-UHFFFAOYSA-N [4-(4-methyl-2-nitroanilino)phenyl]-phenylmethanone Chemical compound [O-][N+](=O)C1=CC(C)=CC=C1NC1=CC=C(C(=O)C=2C=CC=CC=2)C=C1 WPWNGERDPVIMSG-UHFFFAOYSA-N 0.000 description 2
- DZAVJDUZZZKWQR-UHFFFAOYSA-N [4-(5-hydroxy-2-nitroanilino)phenyl]-phenylmethanone Chemical compound OC1=CC=C([N+]([O-])=O)C(NC=2C=CC(=CC=2)C(=O)C=2C=CC=CC=2)=C1 DZAVJDUZZZKWQR-UHFFFAOYSA-N 0.000 description 2
- JAWXAFZYAXDVKU-UHFFFAOYSA-N [4-(n-methyl-2-nitroanilino)phenyl]-phenylmethanone Chemical compound C=1C=CC=C([N+]([O-])=O)C=1N(C)C(C=C1)=CC=C1C(=O)C1=CC=CC=C1 JAWXAFZYAXDVKU-UHFFFAOYSA-N 0.000 description 2
- GLFNJWXUAJALMS-UHFFFAOYSA-N [4-[2-(butylamino)anilino]phenyl]-phenylmethanone Chemical compound CCCCNC1=CC=CC=C1NC1=CC=C(C(=O)C=2C=CC=CC=2)C=C1 GLFNJWXUAJALMS-UHFFFAOYSA-N 0.000 description 2
- SBNJRTQLSNAXBR-UHFFFAOYSA-N [4-[2-(dimethylamino)anilino]phenyl]-phenylmethanone Chemical compound CN(C)C1=CC=CC=C1NC1=CC=C(C(=O)C=2C=CC=CC=2)C=C1 SBNJRTQLSNAXBR-UHFFFAOYSA-N 0.000 description 2
- VNHPXPDRAZIJMK-UHFFFAOYSA-N [4-[2-amino-4-(trifluoromethyl)anilino]phenyl]-phenylmethanone Chemical compound NC1=CC(C(F)(F)F)=CC=C1NC1=CC=C(C(=O)C=2C=CC=CC=2)C=C1 VNHPXPDRAZIJMK-UHFFFAOYSA-N 0.000 description 2
- MSZDUESOGPXQCP-UHFFFAOYSA-N [4-[2-nitro-4-(trifluoromethyl)anilino]phenyl]-phenylmethanone Chemical compound [O-][N+](=O)C1=CC(C(F)(F)F)=CC=C1NC1=CC=C(C(=O)C=2C=CC=CC=2)C=C1 MSZDUESOGPXQCP-UHFFFAOYSA-N 0.000 description 2
- 239000000908 ammonium hydroxide Substances 0.000 description 2
- 239000012300 argon atmosphere Substances 0.000 description 2
- 208000006673 asthma Diseases 0.000 description 2
- OTKPPUXRIADSGD-PPRNARJGSA-N avoparcina Chemical compound O([C@@H]1C2=CC=C(C(=C2)Cl)OC=2C=C3C=C(C=2O[C@H]2C([C@@H](O)[C@H](O)[C@@H](CO)O2)O[C@@H]2O[C@@H](C)[C@H](O)[C@H](N)C2)OC2=CC=C(C=C2)[C@@H](O)[C@H](C(N[C@H](C(=O)N[C@H]3C(=O)N[C@H]2C(=O)N[C@@H]1C(N[C@@H](C1=CC(O)=CC(O)=C1C=1C(O)=CC=C2C=1)C(O)=O)=O)C=1C=CC(O)=CC=1)=O)NC(=O)[C@H](NC)C=1C=CC(O[C@H]2[C@@H]([C@H](O)[C@@H](O)[C@H](C)O2)O)=CC=1)[C@H]1C[C@@H](N)[C@@H](O)[C@H](C)O1 OTKPPUXRIADSGD-PPRNARJGSA-N 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 2
- 238000012512 characterization method Methods 0.000 description 2
- 239000006071 cream Substances 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 239000003937 drug carrier Substances 0.000 description 2
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 2
- 238000005194 fractionation Methods 0.000 description 2
- 210000003714 granulocyte Anatomy 0.000 description 2
- JYGXADMDTFJGBT-VWUMJDOOSA-N hydrocortisone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 JYGXADMDTFJGBT-VWUMJDOOSA-N 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 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 description 2
- 230000003993 interaction Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- PNXSREGEXNJIET-UHFFFAOYSA-N n-[2-(4-benzoylanilino)phenyl]-4-methylbenzenesulfonamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC1=CC=CC=C1NC1=CC=C(C(=O)C=2C=CC=CC=2)C=C1 PNXSREGEXNJIET-UHFFFAOYSA-N 0.000 description 2
- LRGHXTVVOOTKQE-UHFFFAOYSA-N n-[2-(4-benzoylanilino)phenyl]acetamide Chemical compound CC(=O)NC1=CC=CC=C1NC1=CC=C(C(=O)C=2C=CC=CC=2)C=C1 LRGHXTVVOOTKQE-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- WUIDYTPQDTXMJW-UHFFFAOYSA-N n-[2-(4-benzoylanilino)phenyl]formamide Chemical compound O=CNC1=CC=CC=C1NC1=CC=C(C(=O)C=2C=CC=CC=2)C=C1 WUIDYTPQDTXMJW-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- 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 description 2
- YIHBMRONNRSKQH-UHFFFAOYSA-N n-[[4-(2-aminoanilino)phenyl]-phenylmethylidene]hydroxylamine Chemical compound NC1=CC=CC=C1NC1=CC=C(C(=NO)C=2C=CC=CC=2)C=C1 YIHBMRONNRSKQH-UHFFFAOYSA-N 0.000 description 2
- 239000008194 pharmaceutical composition Substances 0.000 description 2
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 2
- 230000003389 potentiating effect Effects 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 206010039073 rheumatoid arthritis Diseases 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- YEENEYXBHNNNGV-XEHWZWQGSA-M sodium;3-acetamido-5-[acetyl(methyl)amino]-2,4,6-triiodobenzoate;(2r,3r,4s,5s,6r)-2-[(2r,3s,4s,5r)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound [Na+].CC(=O)N(C)C1=C(I)C(NC(C)=O)=C(I)C(C([O-])=O)=C1I.O[C@H]1[C@H](O)[C@@H](CO)O[C@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 YEENEYXBHNNNGV-XEHWZWQGSA-M 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- FWPIDFUJEMBDLS-UHFFFAOYSA-L tin(II) chloride dihydrate Chemical compound O.O.Cl[Sn]Cl FWPIDFUJEMBDLS-UHFFFAOYSA-L 0.000 description 2
- 239000002569 water oil cream Substances 0.000 description 2
- OYXUDLWAPMEVHO-UHFFFAOYSA-N (2,4-dichlorophenyl)-[4-(2-nitroanilino)phenyl]methanone Chemical compound [O-][N+](=O)C1=CC=CC=C1NC1=CC=C(C(=O)C=2C(=CC(Cl)=CC=2)Cl)C=C1 OYXUDLWAPMEVHO-UHFFFAOYSA-N 0.000 description 1
- JQXAVAIKFKTDDF-UHFFFAOYSA-N (2-fluorophenyl)-[4-(2-nitroanilino)phenyl]methanone Chemical compound [O-][N+](=O)C1=CC=CC=C1NC1=CC=C(C(=O)C=2C(=CC=CC=2)F)C=C1 JQXAVAIKFKTDDF-UHFFFAOYSA-N 0.000 description 1
- QABMYPIIDFKYMN-UHFFFAOYSA-N (2-methylphenyl)-[4-(2-nitroanilino)phenyl]methanone Chemical compound CC1=CC=CC=C1C(=O)C(C=C1)=CC=C1NC1=CC=CC=C1[N+]([O-])=O QABMYPIIDFKYMN-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- KZOQTFUNZWRDSH-UHFFFAOYSA-N (4-amino-2-chlorophenyl)-(2,6-dimethylphenyl)methanone Chemical compound CC1=CC=CC(C)=C1C(=O)C1=CC=C(N)C=C1Cl KZOQTFUNZWRDSH-UHFFFAOYSA-N 0.000 description 1
- JDPUVXKLXRLLLE-UHFFFAOYSA-N (4-amino-2-chlorophenyl)-(2-methoxyphenyl)methanone Chemical compound COC1=CC=CC=C1C(=O)C1=CC=C(N)C=C1Cl JDPUVXKLXRLLLE-UHFFFAOYSA-N 0.000 description 1
- WIXSUPUXSXRDEZ-UHFFFAOYSA-N (4-amino-2-chlorophenyl)-(4-chlorophenyl)methanone Chemical compound ClC1=CC(N)=CC=C1C(=O)C1=CC=C(Cl)C=C1 WIXSUPUXSXRDEZ-UHFFFAOYSA-N 0.000 description 1
- PTFQDUQPDDCGKW-UHFFFAOYSA-N (4-amino-2-chlorophenyl)-(4-fluoro-2-methylphenyl)methanone Chemical compound CC1=CC(F)=CC=C1C(=O)C1=CC=C(N)C=C1Cl PTFQDUQPDDCGKW-UHFFFAOYSA-N 0.000 description 1
- IALNCLAASQJLLF-UHFFFAOYSA-N (4-amino-2-chlorophenyl)-(4-methoxy-2,6-dimethylphenyl)methanone Chemical compound CC1=CC(OC)=CC(C)=C1C(=O)C1=CC=C(N)C=C1Cl IALNCLAASQJLLF-UHFFFAOYSA-N 0.000 description 1
- FAMPQSYZDRVAOG-UHFFFAOYSA-N (4-amino-2-chlorophenyl)-[2-(trifluoromethyl)phenyl]methanone Chemical compound ClC1=CC(N)=CC=C1C(=O)C1=CC=CC=C1C(F)(F)F FAMPQSYZDRVAOG-UHFFFAOYSA-N 0.000 description 1
- BRFIURZMLORQNB-UHFFFAOYSA-N (4-amino-2-methoxyphenyl)-(2-methylphenyl)methanone Chemical compound COC1=CC(N)=CC=C1C(=O)C1=CC=CC=C1C BRFIURZMLORQNB-UHFFFAOYSA-N 0.000 description 1
- LMYUWPOFHRFDHX-UHFFFAOYSA-N (4-amino-3-chlorophenyl)-phenylmethanone Chemical compound C1=C(Cl)C(N)=CC=C1C(=O)C1=CC=CC=C1 LMYUWPOFHRFDHX-UHFFFAOYSA-N 0.000 description 1
- YBNPGCZJZYYDJF-UHFFFAOYSA-N (4-amino-3-methoxyphenyl)-(2-methylphenyl)methanone Chemical compound C1=C(N)C(OC)=CC(C(=O)C=2C(=CC=CC=2)C)=C1 YBNPGCZJZYYDJF-UHFFFAOYSA-N 0.000 description 1
- QFKHMSPSGVVFPL-UHFFFAOYSA-N (4-amino-3-methylphenyl)-(2-methylphenyl)methanone Chemical compound C1=C(N)C(C)=CC(C(=O)C=2C(=CC=CC=2)C)=C1 QFKHMSPSGVVFPL-UHFFFAOYSA-N 0.000 description 1
- ZCVUMNJAVAXADT-UHFFFAOYSA-N (4-amino-3-methylphenyl)-phenylmethanone Chemical compound C1=C(N)C(C)=CC(C(=O)C=2C=CC=CC=2)=C1 ZCVUMNJAVAXADT-UHFFFAOYSA-N 0.000 description 1
- NGOOFAMQPUEDJM-UHFFFAOYSA-N (4-amino-3-nitrophenyl)-phenylmethanone Chemical compound C1=C([N+]([O-])=O)C(N)=CC=C1C(=O)C1=CC=CC=C1 NGOOFAMQPUEDJM-UHFFFAOYSA-N 0.000 description 1
- CMHCSTQHXYOUES-UHFFFAOYSA-N (4-aminophenyl)-(2,3,5,6-tetramethylphenyl)methanone Chemical compound CC1=CC(C)=C(C)C(C(=O)C=2C=CC(N)=CC=2)=C1C CMHCSTQHXYOUES-UHFFFAOYSA-N 0.000 description 1
- LMIXVPNNEUJDFC-UHFFFAOYSA-N (4-aminophenyl)-(2,3-dihydro-1,4-benzodioxin-6-yl)methanone Chemical compound C1=CC(N)=CC=C1C(=O)C1=CC=C(OCCO2)C2=C1 LMIXVPNNEUJDFC-UHFFFAOYSA-N 0.000 description 1
- YFNJQBAKPSXIRA-UHFFFAOYSA-N (4-aminophenyl)-(2,3-dimethoxyphenyl)methanone Chemical compound COC1=CC=CC(C(=O)C=2C=CC(N)=CC=2)=C1OC YFNJQBAKPSXIRA-UHFFFAOYSA-N 0.000 description 1
- HHFUALNALCAZLO-UHFFFAOYSA-N (4-aminophenyl)-(2,4-dichlorophenyl)methanone Chemical compound C1=CC(N)=CC=C1C(=O)C1=CC=C(Cl)C=C1Cl HHFUALNALCAZLO-UHFFFAOYSA-N 0.000 description 1
- ILHZGRUVBJMSSN-UHFFFAOYSA-N (4-aminophenyl)-(2-bromophenyl)methanone Chemical compound C1=CC(N)=CC=C1C(=O)C1=CC=CC=C1Br ILHZGRUVBJMSSN-UHFFFAOYSA-N 0.000 description 1
- VSKFNHFMZNRVRU-UHFFFAOYSA-N (4-aminophenyl)-(2-chlorophenyl)methanone Chemical compound C1=CC(N)=CC=C1C(=O)C1=CC=CC=C1Cl VSKFNHFMZNRVRU-UHFFFAOYSA-N 0.000 description 1
- QXFCGAZWPFHLST-UHFFFAOYSA-N (4-aminophenyl)-(2-ethylphenyl)methanone Chemical compound CCC1=CC=CC=C1C(=O)C1=CC=C(N)C=C1 QXFCGAZWPFHLST-UHFFFAOYSA-N 0.000 description 1
- FRGXRXKVVAHXBO-UHFFFAOYSA-N (4-aminophenyl)-(2-fluorophenyl)methanone Chemical compound C1=CC(N)=CC=C1C(=O)C1=CC=CC=C1F FRGXRXKVVAHXBO-UHFFFAOYSA-N 0.000 description 1
- RDQHBBCEAXUGGK-UHFFFAOYSA-N (4-aminophenyl)-(2-hydroxyphenyl)methanone Chemical compound C1=CC(N)=CC=C1C(=O)C1=CC=CC=C1O RDQHBBCEAXUGGK-UHFFFAOYSA-N 0.000 description 1
- OVBDCBBDCKTXBA-UHFFFAOYSA-N (4-aminophenyl)-(2-methoxyphenyl)methanone Chemical compound COC1=CC=CC=C1C(=O)C1=CC=C(N)C=C1 OVBDCBBDCKTXBA-UHFFFAOYSA-N 0.000 description 1
- WKLKSQGGMLLLTD-UHFFFAOYSA-N (4-aminophenyl)-(2-phenylphenyl)methanone Chemical compound C1=CC(N)=CC=C1C(=O)C1=CC=CC=C1C1=CC=CC=C1 WKLKSQGGMLLLTD-UHFFFAOYSA-N 0.000 description 1
- JQOPXNXAWAGPKG-UHFFFAOYSA-N (4-aminophenyl)-(3,4,5-trimethoxyphenyl)methanone Chemical compound COC1=C(OC)C(OC)=CC(C(=O)C=2C=CC(N)=CC=2)=C1 JQOPXNXAWAGPKG-UHFFFAOYSA-N 0.000 description 1
- CCRQBZJPINDVSZ-UHFFFAOYSA-N (4-aminophenyl)-(3,5-dichlorophenyl)methanone Chemical compound C1=CC(N)=CC=C1C(=O)C1=CC(Cl)=CC(Cl)=C1 CCRQBZJPINDVSZ-UHFFFAOYSA-N 0.000 description 1
- BPXMYSCPZQVXMA-UHFFFAOYSA-N (4-aminophenyl)-(3-butoxyphenyl)methanone Chemical compound CCCCOC1=CC=CC(C(=O)C=2C=CC(N)=CC=2)=C1 BPXMYSCPZQVXMA-UHFFFAOYSA-N 0.000 description 1
- WMBDFHTYJOXOOL-UHFFFAOYSA-N (4-aminophenyl)-(3-chlorophenyl)methanone Chemical compound C1=CC(N)=CC=C1C(=O)C1=CC=CC(Cl)=C1 WMBDFHTYJOXOOL-UHFFFAOYSA-N 0.000 description 1
- RGINXMPQTJUCOC-UHFFFAOYSA-N (4-aminophenyl)-(3-fluorophenyl)methanone Chemical compound C1=CC(N)=CC=C1C(=O)C1=CC=CC(F)=C1 RGINXMPQTJUCOC-UHFFFAOYSA-N 0.000 description 1
- OCQNVAPDJIPHTF-UHFFFAOYSA-N (4-aminophenyl)-(3-methoxy-4-methylphenyl)methanone Chemical compound C1=C(C)C(OC)=CC(C(=O)C=2C=CC(N)=CC=2)=C1 OCQNVAPDJIPHTF-UHFFFAOYSA-N 0.000 description 1
- IRGUTCABLOCAIL-UHFFFAOYSA-N (4-aminophenyl)-(3-methylphenyl)methanone Chemical compound CC1=CC=CC(C(=O)C=2C=CC(N)=CC=2)=C1 IRGUTCABLOCAIL-UHFFFAOYSA-N 0.000 description 1
- RFDCQSBGTPPYDF-UHFFFAOYSA-N (4-aminophenyl)-(3-phenylphenyl)methanone Chemical compound C1=CC(N)=CC=C1C(=O)C1=CC=CC(C=2C=CC=CC=2)=C1 RFDCQSBGTPPYDF-UHFFFAOYSA-N 0.000 description 1
- JHJFBCGUBHYICK-UHFFFAOYSA-N (4-aminophenyl)-(4-chloro-2-propan-2-ylsulfanylphenyl)methanone Chemical compound CC(C)SC1=CC(Cl)=CC=C1C(=O)C1=CC=C(N)C=C1 JHJFBCGUBHYICK-UHFFFAOYSA-N 0.000 description 1
- BBUQOIDPQZFKKY-UHFFFAOYSA-N (4-aminophenyl)-(4-chlorophenyl)methanone Chemical compound C1=CC(N)=CC=C1C(=O)C1=CC=C(Cl)C=C1 BBUQOIDPQZFKKY-UHFFFAOYSA-N 0.000 description 1
- RZSVJESSJAGPTI-UHFFFAOYSA-N (4-aminophenyl)-(4-ethoxyphenyl)methanone Chemical compound C1=CC(OCC)=CC=C1C(=O)C1=CC=C(N)C=C1 RZSVJESSJAGPTI-UHFFFAOYSA-N 0.000 description 1
- JHRKKHFDXTWUJO-UHFFFAOYSA-N (4-aminophenyl)-(4-fluorophenyl)methanone Chemical compound C1=CC(N)=CC=C1C(=O)C1=CC=C(F)C=C1 JHRKKHFDXTWUJO-UHFFFAOYSA-N 0.000 description 1
- IZSRTZLNLWGKMS-UHFFFAOYSA-N (4-aminophenyl)-(4-methoxyphenyl)methanone Chemical compound C1=CC(OC)=CC=C1C(=O)C1=CC=C(N)C=C1 IZSRTZLNLWGKMS-UHFFFAOYSA-N 0.000 description 1
- JIIOWTMWDBIFRK-UHFFFAOYSA-N (4-aminophenyl)-(4-pentylphenyl)methanone Chemical compound C1=CC(CCCCC)=CC=C1C(=O)C1=CC=C(N)C=C1 JIIOWTMWDBIFRK-UHFFFAOYSA-N 0.000 description 1
- IRZVRLCFUDFBNW-UHFFFAOYSA-N (4-aminophenyl)-(4-phenylmethoxyphenyl)methanone Chemical compound C1=CC(N)=CC=C1C(=O)C(C=C1)=CC=C1OCC1=CC=CC=C1 IRZVRLCFUDFBNW-UHFFFAOYSA-N 0.000 description 1
- VQZHILQXIMVRCH-UHFFFAOYSA-N (4-aminophenyl)-(4-phenylphenyl)methanone Chemical compound C1=CC(N)=CC=C1C(=O)C1=CC=C(C=2C=CC=CC=2)C=C1 VQZHILQXIMVRCH-UHFFFAOYSA-N 0.000 description 1
- RYSJOFRDCLRZGA-UHFFFAOYSA-N (4-aminophenyl)-(4-tert-butylphenyl)methanone Chemical compound C1=CC(C(C)(C)C)=CC=C1C(=O)C1=CC=C(N)C=C1 RYSJOFRDCLRZGA-UHFFFAOYSA-N 0.000 description 1
- OQKDRYIKGKSELX-UHFFFAOYSA-N (4-aminophenyl)-(6-chloro-3,4,6-trifluorocyclohexa-2,4-dien-1-yl)methanone Chemical compound C1=CC(N)=CC=C1C(=O)C1C(Cl)(F)C=C(F)C(F)=C1 OQKDRYIKGKSELX-UHFFFAOYSA-N 0.000 description 1
- WCILXOWAMCZBEV-UHFFFAOYSA-N (4-aminophenyl)-[2-(phenoxymethyl)phenyl]methanone Chemical compound C1=CC(N)=CC=C1C(=O)C1=CC=CC=C1COC1=CC=CC=C1 WCILXOWAMCZBEV-UHFFFAOYSA-N 0.000 description 1
- URMXIPYNMUDHOV-UHFFFAOYSA-N (4-aminophenyl)-[2-[(2-methylpropan-2-yl)oxy]phenyl]methanone Chemical compound CC(C)(C)OC1=CC=CC=C1C(=O)C1=CC=C(N)C=C1 URMXIPYNMUDHOV-UHFFFAOYSA-N 0.000 description 1
- GIWIIQNPULGKSU-UHFFFAOYSA-N (4-aminophenyl)-[3-(dimethylamino)phenyl]methanone Chemical compound CN(C)C1=CC=CC(C(=O)C=2C=CC(N)=CC=2)=C1 GIWIIQNPULGKSU-UHFFFAOYSA-N 0.000 description 1
- PFBXABYFEJCEMY-UHFFFAOYSA-N (4-aminophenyl)-[3-(trifluoromethyl)phenyl]methanone Chemical compound C1=CC(N)=CC=C1C(=O)C1=CC=CC(C(F)(F)F)=C1 PFBXABYFEJCEMY-UHFFFAOYSA-N 0.000 description 1
- LYDZOEBKYJQWSW-UHFFFAOYSA-N (4-aminophenyl)-[4-(trifluoromethyl)phenyl]methanone Chemical compound C1=CC(N)=CC=C1C(=O)C1=CC=C(C(F)(F)F)C=C1 LYDZOEBKYJQWSW-UHFFFAOYSA-N 0.000 description 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 description 1
- 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 description 1
- FWIROFMBWVMWLB-UHFFFAOYSA-N 1-bromo-3-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC(Br)=C1 FWIROFMBWVMWLB-UHFFFAOYSA-N 0.000 description 1
- MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 1
- XUCYJGMIICONES-UHFFFAOYSA-N 1-fluoro-2-methyl-4-nitrobenzene Chemical compound CC1=CC([N+]([O-])=O)=CC=C1F XUCYJGMIICONES-UHFFFAOYSA-N 0.000 description 1
- HLDFCCHSOZWKAA-UHFFFAOYSA-N 1-fluoro-2-nitro-4-(trifluoromethyl)benzene Chemical compound [O-][N+](=O)C1=CC(C(F)(F)F)=CC=C1F HLDFCCHSOZWKAA-UHFFFAOYSA-N 0.000 description 1
- OQURWGJAWSLGQG-UHFFFAOYSA-N 1-isocyanatopropane Chemical compound CCCN=C=O OQURWGJAWSLGQG-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- QTMAZYGAVHCKKX-UHFFFAOYSA-N 2-[(4-amino-5-bromopyrrolo[2,3-d]pyrimidin-7-yl)methoxy]propane-1,3-diol Chemical compound NC1=NC=NC2=C1C(Br)=CN2COC(CO)CO QTMAZYGAVHCKKX-UHFFFAOYSA-N 0.000 description 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 description 1
- DPHCXXYPSYMICK-UHFFFAOYSA-N 2-chloro-1-fluoro-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(F)C(Cl)=C1 DPHCXXYPSYMICK-UHFFFAOYSA-N 0.000 description 1
- ICXSHFWYCHJILC-UHFFFAOYSA-N 2-fluoro-5-nitrobenzoic acid Chemical compound OC(=O)C1=CC([N+]([O-])=O)=CC=C1F ICXSHFWYCHJILC-UHFFFAOYSA-N 0.000 description 1
- YLACBMHBZVYOAP-UHFFFAOYSA-N 2-fluoro-5-nitrobenzonitrile Chemical compound [O-][N+](=O)C1=CC=C(F)C(C#N)=C1 YLACBMHBZVYOAP-UHFFFAOYSA-N 0.000 description 1
- YGIRGDZNWYJEPU-UHFFFAOYSA-N 2-n-[4-(n-methoxy-c-phenylcarbonimidoyl)phenyl]benzene-1,2-diamine Chemical compound C=1C=C(NC=2C(=CC=CC=2)N)C=CC=1C(=NOC)C1=CC=CC=C1 YGIRGDZNWYJEPU-UHFFFAOYSA-N 0.000 description 1
- QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 description 1
- GFRDNMWIOMGGRT-UHFFFAOYSA-N 3-(4-aminobenzoyl)benzonitrile Chemical compound C1=CC(N)=CC=C1C(=O)C1=CC=CC(C#N)=C1 GFRDNMWIOMGGRT-UHFFFAOYSA-N 0.000 description 1
- CLFWCXMAXAWQDH-UHFFFAOYSA-N 3-amino-4-(4-benzoylanilino)benzoic acid Chemical compound NC1=CC(C(O)=O)=CC=C1NC1=CC=C(C(=O)C=2C=CC=CC=2)C=C1 CLFWCXMAXAWQDH-UHFFFAOYSA-N 0.000 description 1
- CSSGKHVRDGATJL-UHFFFAOYSA-N 3-fluoro-4-nitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C(F)=C1 CSSGKHVRDGATJL-UHFFFAOYSA-N 0.000 description 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
- GVCLNACSYKYUHP-UHFFFAOYSA-N 4-amino-7-(2-hydroxyethoxymethyl)pyrrolo[2,3-d]pyrimidine-5-carbothioamide Chemical compound C1=NC(N)=C2C(C(=S)N)=CN(COCCO)C2=N1 GVCLNACSYKYUHP-UHFFFAOYSA-N 0.000 description 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 description 1
- BOJWTAQWPVBIPG-UHFFFAOYSA-N 4-fluoro-3-nitrobenzoic acid Chemical compound OC(=O)C1=CC=C(F)C([N+]([O-])=O)=C1 BOJWTAQWPVBIPG-UHFFFAOYSA-N 0.000 description 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 description 1
- NJIAKNWTIVDSDA-FQEVSTJZSA-N 7-[4-(1-methylsulfonylpiperidin-4-yl)phenyl]-n-[[(2s)-morpholin-2-yl]methyl]pyrido[3,4-b]pyrazin-5-amine Chemical compound C1CN(S(=O)(=O)C)CCC1C1=CC=C(C=2N=C(NC[C@H]3OCCNC3)C3=NC=CN=C3C=2)C=C1 NJIAKNWTIVDSDA-FQEVSTJZSA-N 0.000 description 1
- 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 description 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 description 1
- 201000001320 Atherosclerosis Diseases 0.000 description 1
- 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 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 1
- 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 description 1
- UHNRLQRZRNKOKU-UHFFFAOYSA-N CCN(CC1=NC2=C(N1)C1=CC=C(C=C1N=C2N)C1=NNC=C1)C(C)=O Chemical compound CCN(CC1=NC2=C(N1)C1=CC=C(C=C1N=C2N)C1=NNC=C1)C(C)=O UHNRLQRZRNKOKU-UHFFFAOYSA-N 0.000 description 1
- SCJNYBYSTCRPAO-LXBQGUBHSA-N CN(C)C\C=C\C(=O)NC1=CC=C(N=C1)C(=O)N[C@@]1(C)CCC[C@H](C1)NC1=NC(C2=CNC3=CC=CC=C23)=C(Cl)C=N1 Chemical compound CN(C)C\C=C\C(=O)NC1=CC=C(N=C1)C(=O)N[C@@]1(C)CCC[C@H](C1)NC1=NC(C2=CNC3=CC=CC=C23)=C(Cl)C=N1 SCJNYBYSTCRPAO-LXBQGUBHSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 1
- 206010012442 Dermatitis contact Diseases 0.000 description 1
- 229920002307 Dextran Polymers 0.000 description 1
- 238000002965 ELISA Methods 0.000 description 1
- 241000792859 Enema Species 0.000 description 1
- 201000005569 Gout Diseases 0.000 description 1
- 206010020751 Hypersensitivity Diseases 0.000 description 1
- 208000022559 Inflammatory bowel disease Diseases 0.000 description 1
- 102000015696 Interleukins Human genes 0.000 description 1
- 108010063738 Interleukins Proteins 0.000 description 1
- 229940121948 Muscarinic receptor antagonist Drugs 0.000 description 1
- 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 description 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 description 1
- 125000003001 N-formyl-L-methionyl group Chemical group O=C([H])N([H])[C@]([H])(C(=O)[*])C([H])([H])C([H])([H])SC([H])([H])[H] 0.000 description 1
- PRQROPMIIGLWRP-UHFFFAOYSA-N N-formyl-methionyl-leucyl-phenylalanin Chemical compound CSCCC(NC=O)C(=O)NC(CC(C)C)C(=O)NC(C(O)=O)CC1=CC=CC=C1 PRQROPMIIGLWRP-UHFFFAOYSA-N 0.000 description 1
- CMWTZPSULFXXJA-UHFFFAOYSA-N Naproxen Natural products C1=C(C(C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-UHFFFAOYSA-N 0.000 description 1
- 239000005662 Paraffin oil Substances 0.000 description 1
- 108010003541 Platelet Activating Factor Proteins 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 239000012980 RPMI-1640 medium Substances 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 201000002661 Spondylitis Diseases 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 102000019197 Superoxide Dismutase Human genes 0.000 description 1
- 108010012715 Superoxide dismutase Proteins 0.000 description 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
- DRBWRJPFNOBNIO-KOLCDFICSA-N [(2r)-1-[(2r)-2-(pyridine-4-carbonylamino)propanoyl]pyrrolidin-2-yl]boronic acid Chemical compound N([C@H](C)C(=O)N1[C@@H](CCC1)B(O)O)C(=O)C1=CC=NC=C1 DRBWRJPFNOBNIO-KOLCDFICSA-N 0.000 description 1
- RRNRLVPCGYTZJQ-UHFFFAOYSA-N [2-chloro-4-(2-nitroanilino)phenyl]-(2,6-dimethylphenyl)methanone Chemical compound CC1=CC=CC(C)=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1[N+]([O-])=O RRNRLVPCGYTZJQ-UHFFFAOYSA-N 0.000 description 1
- ZQPFTMYFLNUBTM-UHFFFAOYSA-N [4-(2-amino-4-nitroanilino)phenyl]-phenylmethanone Chemical compound NC1=CC([N+]([O-])=O)=CC=C1NC1=CC=C(C(=O)C=2C=CC=CC=2)C=C1 ZQPFTMYFLNUBTM-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 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 description 1
- 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 description 1
- PFTFXCYRFQKXMN-UHFFFAOYSA-N [4-(2-aminoanilino)phenyl]-(2-methoxyphenyl)methanone Chemical compound COC1=CC=CC=C1C(=O)C(C=C1)=CC=C1NC1=CC=CC=C1N PFTFXCYRFQKXMN-UHFFFAOYSA-N 0.000 description 1
- IZJMWKZLWGKLSR-UHFFFAOYSA-N [4-(2-aminoanilino)phenyl]-(3-fluorophenyl)methanone Chemical compound NC1=CC=CC=C1NC1=CC=C(C(=O)C=2C=C(F)C=CC=2)C=C1 IZJMWKZLWGKLSR-UHFFFAOYSA-N 0.000 description 1
- VDKRYSKRXSNRGS-UHFFFAOYSA-N [4-(2-aminoanilino)phenyl]-(3-methylphenyl)methanone Chemical compound CC1=CC=CC(C(=O)C=2C=CC(NC=3C(=CC=CC=3)N)=CC=2)=C1 VDKRYSKRXSNRGS-UHFFFAOYSA-N 0.000 description 1
- ANXNCEKZPLFBIY-UHFFFAOYSA-N [4-(2-aminoanilino)phenyl]-(4-methoxyphenyl)methanone Chemical compound C1=CC(OC)=CC=C1C(=O)C(C=C1)=CC=C1NC1=CC=CC=C1N ANXNCEKZPLFBIY-UHFFFAOYSA-N 0.000 description 1
- BNLTXCMBLXQAEH-UHFFFAOYSA-N [4-(2-aminoanilino)phenyl]-[3-(dimethylamino)phenyl]methanone Chemical compound CN(C)C1=CC=CC(C(=O)C=2C=CC(NC=3C(=CC=CC=3)N)=CC=2)=C1 BNLTXCMBLXQAEH-UHFFFAOYSA-N 0.000 description 1
- IBWVRJMOAVMFQO-UHFFFAOYSA-N [4-(2-aminoanilino)phenyl]-[3-(trifluoromethyl)phenyl]methanone Chemical compound NC1=CC=CC=C1NC1=CC=C(C(=O)C=2C=C(C=CC=2)C(F)(F)F)C=C1 IBWVRJMOAVMFQO-UHFFFAOYSA-N 0.000 description 1
- YQSPGYDNOFZEMC-UHFFFAOYSA-N [4-(2-aminoanilino)phenyl]-[4-(trifluoromethyl)phenyl]methanone Chemical compound NC1=CC=CC=C1NC1=CC=C(C(=O)C=2C=CC(=CC=2)C(F)(F)F)C=C1 YQSPGYDNOFZEMC-UHFFFAOYSA-N 0.000 description 1
- IMEOMNXDZVTHRD-UHFFFAOYSA-N [4-(2-nitroanilino)phenyl]-(4-pentan-2-yloxyphenyl)methanone Chemical compound C1=CC(OC(C)CCC)=CC=C1C(=O)C(C=C1)=CC=C1NC1=CC=CC=C1[N+]([O-])=O IMEOMNXDZVTHRD-UHFFFAOYSA-N 0.000 description 1
- PIWXMQUHYNUSDG-UHFFFAOYSA-N [4-(4-amino-2-chloroanilino)phenyl]-phenylmethanone Chemical compound ClC1=CC(N)=CC=C1NC1=CC=C(C(=O)C=2C=CC=CC=2)C=C1 PIWXMQUHYNUSDG-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 239000000464 adrenergic agent Substances 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 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 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 208000002029 allergic contact dermatitis Diseases 0.000 description 1
- 230000007815 allergy Effects 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 229940124599 anti-inflammatory drug Drugs 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 239000003529 anticholesteremic agent Substances 0.000 description 1
- 229940127226 anticholesterol agent Drugs 0.000 description 1
- 229940125715 antihistaminic agent Drugs 0.000 description 1
- 239000000739 antihistaminic agent Substances 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 238000001574 biopsy Methods 0.000 description 1
- 229940098773 bovine serum albumin Drugs 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 244000309466 calf Species 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000012560 cell impurity Substances 0.000 description 1
- 229940082500 cetostearyl alcohol Drugs 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 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 description 1
- 239000000812 cholinergic antagonist Substances 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 208000010247 contact dermatitis Diseases 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 1
- 230000016396 cytokine production Effects 0.000 description 1
- 230000009089 cytolysis Effects 0.000 description 1
- 229920006237 degradable polymer Polymers 0.000 description 1
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 1
- 229940075557 diethylene glycol monoethyl ether Drugs 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000007920 enema Substances 0.000 description 1
- 229940095399 enema Drugs 0.000 description 1
- 210000003743 erythrocyte Anatomy 0.000 description 1
- FRYHCSODNHYDPU-UHFFFAOYSA-N ethanesulfonyl chloride Chemical compound CCS(Cl)(=O)=O FRYHCSODNHYDPU-UHFFFAOYSA-N 0.000 description 1
- DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 1
- PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 229940067594 flufenamate Drugs 0.000 description 1
- LPEPZBJOKDYZAD-UHFFFAOYSA-N flufenamic acid Chemical compound OC(=O)C1=CC=CC=C1NC1=CC=CC(C(F)(F)F)=C1 LPEPZBJOKDYZAD-UHFFFAOYSA-N 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- 239000003862 glucocorticoid Substances 0.000 description 1
- 150000002343 gold Chemical class 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000009775 high-speed stirring Methods 0.000 description 1
- WJLFHDKAOYPRJZ-UHFFFAOYSA-N hydrazine;dihydrate Chemical compound O.O.NN.NN WJLFHDKAOYPRJZ-UHFFFAOYSA-N 0.000 description 1
- 229960000890 hydrocortisone Drugs 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 229960000905 indomethacin Drugs 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 229940047122 interleukins Drugs 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- MLRAALKFHIREQS-UHFFFAOYSA-N iodo(iodomethylsulfinyl)methane Chemical compound ICS(=O)CI MLRAALKFHIREQS-UHFFFAOYSA-N 0.000 description 1
- 235000015110 jellies Nutrition 0.000 description 1
- 229940040145 liniment Drugs 0.000 description 1
- 239000000865 liniment Substances 0.000 description 1
- 239000002502 liposome Substances 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
- 229960002216 methylparaben Drugs 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 210000005087 mononuclear cell Anatomy 0.000 description 1
- 210000000214 mouth Anatomy 0.000 description 1
- OBEXUAPBTUTPDV-UHFFFAOYSA-N n-(4-benzoylphenyl)acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1C(=O)C1=CC=CC=C1 OBEXUAPBTUTPDV-UHFFFAOYSA-N 0.000 description 1
- IHCHOVVAJBADAH-UHFFFAOYSA-N n-[2-hydroxy-4-(1h-pyrazol-4-yl)phenyl]-6-methoxy-3,4-dihydro-2h-chromene-3-carboxamide Chemical compound C1C2=CC(OC)=CC=C2OCC1C(=O)NC(C(=C1)O)=CC=C1C=1C=NNC=1 IHCHOVVAJBADAH-UHFFFAOYSA-N 0.000 description 1
- LPOIGVZLNWEGJG-UHFFFAOYSA-N n-benzyl-5-(4-methylpiperazin-1-yl)-2-nitroaniline Chemical compound C1CN(C)CCN1C1=CC=C([N+]([O-])=O)C(NCC=2C=CC=CC=2)=C1 LPOIGVZLNWEGJG-UHFFFAOYSA-N 0.000 description 1
- 229960002009 naproxen Drugs 0.000 description 1
- 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 description 1
- 210000003928 nasal cavity Anatomy 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 230000008506 pathogenesis Effects 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 229960001639 penicillamine Drugs 0.000 description 1
- 210000005259 peripheral blood Anatomy 0.000 description 1
- 239000011886 peripheral blood Substances 0.000 description 1
- 210000003819 peripheral blood mononuclear cell Anatomy 0.000 description 1
- 239000008024 pharmaceutical diluent Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229960005323 phenoxyethanol Drugs 0.000 description 1
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
- PHEDXBVPIONUQT-RGYGYFBISA-N phorbol 13-acetate 12-myristate Chemical compound C([C@]1(O)C(=O)C(C)=C[C@H]1[C@@]1(O)[C@H](C)[C@H]2OC(=O)CCCCCCCCCCCCC)C(CO)=C[C@H]1[C@H]1[C@]2(OC(C)=O)C1(C)C PHEDXBVPIONUQT-RGYGYFBISA-N 0.000 description 1
- 230000002062 proliferating effect Effects 0.000 description 1
- 239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
- 229960003415 propylparaben Drugs 0.000 description 1
- 150000003873 salicylate salts Chemical class 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 208000017520 skin disease Diseases 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- KSAVQLQVUXSOCR-UHFFFAOYSA-M sodium lauroyl sarcosinate Chemical compound [Na+].CCCCCCCCCCCC(=O)N(C)CC([O-])=O KSAVQLQVUXSOCR-UHFFFAOYSA-M 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 210000000952 spleen Anatomy 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- NCEXYHBECQHGNR-QZQOTICOSA-N sulfasalazine Chemical compound C1=C(O)C(C(=O)O)=CC(\N=N\C=2C=CC(=CC=2)S(=O)(=O)NC=2N=CC=CC=2)=C1 NCEXYHBECQHGNR-QZQOTICOSA-N 0.000 description 1
- 229960001940 sulfasalazine Drugs 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 238000007910 systemic administration Methods 0.000 description 1
- 229940037128 systemic glucocorticoids Drugs 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- OULAJFUGPPVRBK-UHFFFAOYSA-N tetratriacontyl alcohol Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCO OULAJFUGPPVRBK-UHFFFAOYSA-N 0.000 description 1
- 210000001541 thymus gland Anatomy 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 150000003710 vitamin D derivatives Chemical class 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
Images
Classifications
-
- 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
-
- 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
-
- 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]
-
- 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)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Rheumatology (AREA)
- Pulmonology (AREA)
- Dermatology (AREA)
- Cardiology (AREA)
- Pain & Pain Management (AREA)
- Urology & Nephrology (AREA)
- Heart & Thoracic Surgery (AREA)
- Vascular Medicine (AREA)
- Immunology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (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 |
|---|---|---|---|
| GBGB9701453.4A GB9701453D0 (en) | 1997-01-24 | 1997-01-24 | Aminobenzophenones |
| GB9701453.4 | 1997-01-24 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU99118221A RU99118221A (ru) | 2001-06-27 |
| RU2200153C2 true RU2200153C2 (ru) | 2003-03-10 |
Family
ID=10806523
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU99118221/04A RU2200153C2 (ru) | 1997-01-24 | 1998-01-08 | Аминобензофеноны, способ их получения, фармацевтический препарат, способ лечения и профилактики воспалительных заболеваний кожи |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US6313174B1 (https=) |
| EP (1) | EP0966424B1 (https=) |
| JP (1) | JP4250204B2 (https=) |
| KR (1) | KR100544046B1 (https=) |
| CN (1) | CN1188388C (https=) |
| AT (1) | ATE269844T1 (https=) |
| AU (1) | AU733561B2 (https=) |
| CA (1) | CA2278798C (https=) |
| DE (1) | DE69824705T2 (https=) |
| DK (1) | DK0966424T3 (https=) |
| ES (1) | ES2223116T3 (https=) |
| GB (1) | GB9701453D0 (https=) |
| HU (1) | HUP0000678A3 (https=) |
| NZ (1) | NZ336754A (https=) |
| PL (1) | PL334806A1 (https=) |
| PT (1) | PT966424E (https=) |
| RO (1) | RO120195B1 (https=) |
| RU (1) | RU2200153C2 (https=) |
| WO (1) | WO1998032730A1 (https=) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1210320B1 (en) * | 1999-07-16 | 2004-09-29 | Leo Pharma A/S | Aminobenzophenones as inhibitors of il-1beta and tnf-alpha |
| US6897236B1 (en) | 1999-07-16 | 2005-05-24 | Leo Pharmaceutical Products, Ltd. | Aminobenzophenones as inhibitors of IL-1β and TNF-α |
| AU768512B2 (en) * | 1999-07-16 | 2003-12-18 | Leo Pharmaceutical Products Ltd. A/S (Lovens Kemiske Fabrik Produktionsaktieselskab) | Aminobenzophenones as inhibitors of IL-1beta and TNF-alpha |
| KR20020013961A (ko) | 1999-07-16 | 2002-02-21 | 룬딩 에른스트 | 신규한 아미노벤조페논 |
| US6555710B1 (en) * | 1999-07-16 | 2003-04-29 | Leo Pharmaceutical Products Ltd A/S Lovens Kemiske Fabrik Produktionsaktieselskab | Aminobenzophenones as inhibitors of IL-1 β and TNF-α |
| DE60014681T2 (de) * | 1999-07-16 | 2006-02-02 | Leo Pharma A/S | Aminobenzophenone als inhibitoren von il-1beta und tnf-alpha |
| ATE362912T1 (de) * | 1999-12-06 | 2007-06-15 | Leo Pharma As | Aminobenzophenone als inhibitoren von il-1beta und tnf-alpha |
| EP1250332A1 (en) * | 1999-12-17 | 2002-10-23 | Abbott Laboratories | Inhibitors of interleukin 5 gene expression |
| EP1246823A1 (en) * | 1999-12-28 | 2002-10-09 | Pharmacopeia, Inc. | Pyrimidine and triazine kinase inhibitors |
| 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 |
| 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 |
| WO2002083622A2 (en) * | 2001-04-10 | 2002-10-24 | Leo Pharma A/S | Novel aminophenyl ketone derivatives |
| EP1423356A2 (en) * | 2001-08-28 | 2004-06-02 | Leo Pharma A/S | Novel aminobenzoephenones |
| 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 |
| ES2341473T3 (es) * | 2004-12-13 | 2010-06-21 | Leo Pharma A/S | Compuestos de aminobenzofenona sustituida con triazol. |
| 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 |
| KR102079404B1 (ko) | 2011-08-19 | 2020-02-19 | 더 리젠츠 오브 더 유니버시티 오브 캘리포니아 | 메타-치환된 비페닐 말초 제한형 faah 억제제 |
| ES2908240T3 (es) | 2014-04-07 | 2022-04-28 | Univ California | Inhibidores de la enzima amida hidrolasa de ácidos grasos (FAAH) con biodisponibilidad oral mejorada y su uso como medicamentos |
Citations (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 |
| DE3739402C2 (de) * | 1986-11-21 | 1989-01-12 | Ricoh Kk | Faerbende phthalid-verbindungen, verfahren zu ihrer herstellung und diese enthaltende aufzeichnungsmaterialien |
-
1997
- 1997-01-24 GB GBGB9701453.4A patent/GB9701453D0/en active Pending
-
1998
- 1998-01-08 AU AU54781/98A patent/AU733561B2/en not_active Ceased
- 1998-01-08 HU HU0000678A patent/HUP0000678A3/hu unknown
- 1998-01-08 CN CNB988028301A patent/CN1188388C/zh not_active Expired - Fee Related
- 1998-01-08 EP EP98900270A patent/EP0966424B1/en not_active Expired - Lifetime
- 1998-01-08 PL PL98334806A patent/PL334806A1/xx not_active IP Right Cessation
- 1998-01-08 AT AT98900270T patent/ATE269844T1/de active
- 1998-01-08 RU RU99118221/04A patent/RU2200153C2/ru not_active IP Right Cessation
- 1998-01-08 JP JP53149998A patent/JP4250204B2/ja not_active Expired - Fee Related
- 1998-01-08 KR KR1019997006672A patent/KR100544046B1/ko not_active Expired - Fee Related
- 1998-01-08 NZ NZ336754A patent/NZ336754A/xx not_active IP Right Cessation
- 1998-01-08 ES ES98900270T patent/ES2223116T3/es not_active Expired - Lifetime
- 1998-01-08 DK DK98900270T patent/DK0966424T3/da active
- 1998-01-08 DE DE69824705T patent/DE69824705T2/de not_active Expired - Lifetime
- 1998-01-08 CA CA002278798A patent/CA2278798C/en not_active Expired - Fee Related
- 1998-01-08 RO RO99-00839A patent/RO120195B1/ro unknown
- 1998-01-08 US US09/341,923 patent/US6313174B1/en not_active Expired - Fee Related
- 1998-01-08 WO PCT/DK1998/000008 patent/WO1998032730A1/en not_active Ceased
- 1998-01-08 PT PT98900270T patent/PT966424E/pt unknown
Patent Citations (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 |
| DE3739402C2 (de) * | 1986-11-21 | 1989-01-12 | Ricoh Kk | Faerbende phthalid-verbindungen, verfahren zu ihrer herstellung und diese enthaltende aufzeichnungsmaterialien |
Also Published As
| Publication number | Publication date |
|---|---|
| US6313174B1 (en) | 2001-11-06 |
| AU733561B2 (en) | 2001-05-17 |
| HUP0000678A3 (en) | 2001-11-28 |
| DK0966424T3 (da) | 2004-11-01 |
| EP0966424A1 (en) | 1999-12-29 |
| HK1025306A1 (en) | 2000-11-10 |
| RO120195B1 (ro) | 2005-10-28 |
| CA2278798A1 (en) | 1998-07-30 |
| DE69824705T2 (de) | 2005-07-07 |
| CN1188388C (zh) | 2005-02-09 |
| KR20000070437A (ko) | 2000-11-25 |
| PL334806A1 (en) | 2000-03-13 |
| NZ336754A (en) | 2001-03-30 |
| WO1998032730A1 (en) | 1998-07-30 |
| ATE269844T1 (de) | 2004-07-15 |
| ES2223116T3 (es) | 2005-02-16 |
| PT966424E (pt) | 2004-09-30 |
| DE69824705D1 (de) | 2004-07-29 |
| HUP0000678A2 (hu) | 2001-10-28 |
| EP0966424B1 (en) | 2004-06-23 |
| JP2001511771A (ja) | 2001-08-14 |
| JP4250204B2 (ja) | 2009-04-08 |
| CA2278798C (en) | 2007-07-03 |
| KR100544046B1 (ko) | 2006-01-23 |
| CN1248966A (zh) | 2000-03-29 |
| GB9701453D0 (en) | 1997-03-12 |
| AU5478198A (en) | 1998-08-18 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| RU2200153C2 (ru) | Аминобензофеноны, способ их получения, фармацевтический препарат, способ лечения и профилактики воспалительных заболеваний кожи | |
| KR100395280B1 (ko) | 신규한3환성화합물및그를함유하는의약조성물 | |
| US6262112B1 (en) | Aryl sulfonamides and analogues thereof and their use in the treatment of neurodegenerative diseases | |
| JP3894949B2 (ja) | 抗アテローム性動脈硬化症ジアリール化合物 | |
| US6555710B1 (en) | Aminobenzophenones as inhibitors of IL-1 β and TNF-α | |
| JP4571863B2 (ja) | 抗痛覚過敏剤として有用なキナゾリノン誘導体 | |
| EP0617010B1 (en) | Therapeutic compounds | |
| HUP0201846A2 (en) | Amonobenzophenones as inhibitors of il-1betha and tnf-alpha and pharmaceutical compositions containing them | |
| RU2240995C2 (ru) | Аминобензофеноны в качестве ингибиторов интерлейкина il-1бета и фактора некроза опухолей tnf-альфа | |
| US6750253B1 (en) | Aminobenzophenones as inhibitors of il-1β and tnf-α | |
| RS50886B (sr) | Nova jedinjenja koja su jaki inhibitori mehanizma za izmenu na+/ca2+ i korisni su kod lečenja aritmija | |
| EP3611158A1 (en) | 1,3-di-oxo-indene derivative, pharmaceutically acceptable salt or optical isomer thereof, preparation method thereof, and pharmaceutical composition containing same as an antiviral, active ingredient | |
| CZ259899A3 (cs) | Aminobenzofenony jako inhibitory interleukinu a TNF | |
| EP0924202B1 (en) | Imidazole derivative and medicine comprising the same as active ingredient | |
| Kukolja et al. | Substances Acting on the Central Nervous System. IV. Derivatives of 2-Ethyl-2-phenylbutyramide | |
| JPWO2001016091A1 (ja) | ビスシクロプロパンカルボン酸アミド化合物およびその医薬用途 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | The patent is invalid due to non-payment of fees |
Effective date: 20130109 |