Aminobenzophenones as inhibitors of IL-1 bata and TNF-alpha
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A technology of amino and phenylamino, which is applied in the field of aminobenzophenone as an inhibitor of IL-1β and TNF-α, can solve the problems of undescribed applications and the like
Inactive Publication Date: 2002-09-11
LEO PHARMA PROD LTD AS LOVENS CHEM FAB PRODUKTIONS AS
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[0011] In the compounds of the present invention, it is preferred that R 1 Represent one or more identical or different substituents selected from the group consisting of fluorine, chlorine, bromine, hydroxyl, trifluoromethyl, amino, (C 1 ~C 2 ) alkyl, (C 2 ~C 3 ) alkenyl, (C 1 ~C 3 ) alkoxy, (C 1 ~C 3 ) alkoxycarbonyl, cyano or -CONH 2 ; 2 Represent one or more identical or different substituents selected from the group consisting of hydrogen, fluorine, chlorine, bromine, hydroxyl, trifluoromethyl, amino, (C 1 ~C 3 ) alkyl, (C 2 ~C 3 ) alkenyl, (C 1 ~C 3 ) alkoxy; R 3 Represent one or more identical or different substituents selected from the group consisting of hydrogen, fluorine, chlorine, bromine, hydroxyl, trifluoromethyl, (C 1 ~C 3 ) alkyl, (C 2 ~C 3 ) alkenyl, (C 1 ~C 3 ) alkoxy, (C 1 ~C 3 ) alkoxycarbonyl, cyano, carboxyl or -CONH 2 ; 4 represents hydrogen, (C 1 ~C 2 ) alkyl or allyl; X represents oxygen.
[0012] More preferred are compounds...
Embodiment 1
[0085] EXAMPLES General Procedures, Preparations and Examples
[0086]Specific examples of compounds of formula I are listed in Table 2. All melting points are uncorrected. for 1 H and 13 For C nuclear magnetic resonance (NMR) spectra (300 MHz), unless otherwise stated, the mentioned chemical shifts (δ) (expressed in ppm) are relative to deuteriochloroform and hexadeuterodimethylsulfoxide relative to the internal standard tetramethyl Silane (δ0.00) or chloroform ( 1 H NMRδ7.25, 13 C NMR δ 76.81). Unless a range is mentioned (s singlet, b broad), values are given for multiplets (m) (located around the midpoint), or [doublet (d), triplet (t), quartet peak (q)] or not specified. The organic solvents used were all anhydrous. The term "chromatography" denotes column chromatography using the flash technique and carried out on silica gel.
[0087] The following abbreviations are used in this description:
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Abstract
The present invention relates to compounds of formula (I), wherein R1 and R2 independently represent one or more identical or different substituents selected from the following group: halogen, hydroxyl, mercapto, trifluoromethyl, amino, (C1~C3 )alkyl, (C2~C3) alkenyl, (C1~C3) alkoxy, (C1~C3) alkylthio, (C1~C6) alkylamino, (C1~C3) alkoxycarbonyl, cyano , carbamoyl, phenyl or nitro; further, R2 represents hydrogen; R3 represents hydrogen, halogen, hydroxyl, mercapto, trifluoromethyl, amino, (C1~C3) alkyl, (C2~C3) alkenyl , (C1~C3) alkoxy, (C1~C3) alkylthio, (C1~C6) alkylamino, (C1~C3) alkoxycarbonyl, phenyl, cyano, carboxyl or carbamoyl; R4 represents hydrogen, (C1~C3) alkyl or allyl; (2-methylbenzoyl)-phenylamino]-phenyl]acetamide, where R1 is 2-methyl, R2 is 2-chloro, R3 and R4 are hydrogen, and X is oxygen, and its drugs Acceptable acid salts, hydrates or solvates. The compounds are valuable in human and veterinary medicine.
Description
field of invention [0001] The present invention relates to a class of hitherto unknown compounds showing anti-inflammatory effects, to pharmaceutical preparations containing these compounds, also to unit doses of the preparations, and to their use in the treatment and prevention of the following diseases: asthma, allergy, Arthritis (including rheumatoid arthritis and spondyloarthritis), gout, atherosclerosis, chronic inflammatory bowel disease (crohn's disease), hyperplastic and inflammatory skin disorders (such as psoriasis and atopic dermatitis) , uveitis, septic shock, AIDS and acne. Background of the invention [0002] Previously, a series of closely related aminobenzophenones [eg, 4-(2-amino-4- nitrophenylamino)benzophenone]. However, their application is not described. PCT / DK98 / 00008 discloses aminobenzophenone inhibitors of interleukin 1β (IL-1β) and tumor necrosis factor (TNF-α) secreted in vitro, which may be useful in the treatment of inflammatory diseases such...
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