JP2003516377A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2003516377A5 JP2003516377A5 JP2001543491A JP2001543491A JP2003516377A5 JP 2003516377 A5 JP2003516377 A5 JP 2003516377A5 JP 2001543491 A JP2001543491 A JP 2001543491A JP 2001543491 A JP2001543491 A JP 2001543491A JP 2003516377 A5 JP2003516377 A5 JP 2003516377A5
- Authority
- JP
- Japan
- Prior art keywords
- chloro
- compound
- phenylamino
- methyl
- methylbenzophenone
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 150000001875 compounds Chemical class 0.000 description 150
- -1 hydroxy, mercapto Chemical class 0.000 description 37
- 125000001424 substituent group Chemical group 0.000 description 20
- 229910052739 hydrogen Inorganic materials 0.000 description 17
- 239000001257 hydrogen Substances 0.000 description 17
- 238000000034 method Methods 0.000 description 17
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 14
- 239000004480 active ingredient Substances 0.000 description 13
- 150000001336 alkenes Chemical group 0.000 description 13
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 12
- 125000001153 fluoro group Chemical group F* 0.000 description 12
- 229910052736 halogen Inorganic materials 0.000 description 12
- 150000002367 halogens Chemical class 0.000 description 12
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 11
- 125000004093 cyano group Chemical group *C#N 0.000 description 10
- 150000002431 hydrogen Chemical class 0.000 description 10
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 9
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 9
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 9
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 8
- 229910052760 oxygen Inorganic materials 0.000 description 8
- 239000001301 oxygen Substances 0.000 description 8
- 150000003839 salts Chemical class 0.000 description 8
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 7
- 239000003937 drug carrier Substances 0.000 description 7
- 125000004455 (C1-C3) alkylthio group Chemical group 0.000 description 6
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 description 6
- 125000001309 chloro group Chemical group Cl* 0.000 description 6
- 201000010099 disease Diseases 0.000 description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 6
- 125000001183 hydrocarbyl group Chemical group 0.000 description 6
- 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 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 125000002950 monocyclic group Chemical group 0.000 description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 6
- 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 5
- 108010003541 Platelet Activating Factor Proteins 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 150000004677 hydrates Chemical class 0.000 description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 5
- 239000012453 solvate Substances 0.000 description 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 4
- 239000005711 Benzoic acid Substances 0.000 description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 235000010233 benzoic acid Nutrition 0.000 description 4
- 241000894007 species Species 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- 239000011593 sulfur Chemical group 0.000 description 4
- 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 3
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 description 3
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 3
- 125000006592 (C2-C3) alkenyl group Chemical group 0.000 description 3
- PFWLFWPASULGAN-UHFFFAOYSA-N 7-methylxanthine Chemical compound N1C(=O)NC(=O)C2=C1N=CN2C PFWLFWPASULGAN-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 201000001320 Atherosclerosis Diseases 0.000 description 3
- 208000011231 Crohn disease Diseases 0.000 description 3
- 201000004624 Dermatitis Diseases 0.000 description 3
- 201000005569 Gout Diseases 0.000 description 3
- 206010020751 Hypersensitivity Diseases 0.000 description 3
- 208000022559 Inflammatory bowel disease Diseases 0.000 description 3
- 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 3
- 201000004681 Psoriasis Diseases 0.000 description 3
- 206010040070 Septic Shock Diseases 0.000 description 3
- 206010046851 Uveitis Diseases 0.000 description 3
- 125000004414 alkyl thio group Chemical group 0.000 description 3
- 208000026935 allergic disease Diseases 0.000 description 3
- 230000007815 allergy Effects 0.000 description 3
- 239000005557 antagonist Substances 0.000 description 3
- 230000001078 anti-cholinergic effect Effects 0.000 description 3
- 239000003529 anticholesteremic agent Substances 0.000 description 3
- 229940127226 anticholesterol agent Drugs 0.000 description 3
- 239000000739 antihistaminic agent Substances 0.000 description 3
- 206010003246 arthritis Diseases 0.000 description 3
- 208000006673 asthma Diseases 0.000 description 3
- 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 3
- 230000001684 chronic effect Effects 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 229940067594 flufenamate Drugs 0.000 description 3
- 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 3
- 239000003862 glucocorticoid Substances 0.000 description 3
- 229960000905 indomethacin Drugs 0.000 description 3
- 229960002009 naproxen Drugs 0.000 description 3
- 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 3
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 3
- 229960001639 penicillamine Drugs 0.000 description 3
- 239000008194 pharmaceutical composition Substances 0.000 description 3
- 230000002062 proliferating effect Effects 0.000 description 3
- 206010039073 rheumatoid arthritis Diseases 0.000 description 3
- 230000036303 septic shock Effects 0.000 description 3
- 201000005671 spondyloarthropathy Diseases 0.000 description 3
- 150000003751 zinc Chemical class 0.000 description 3
- VDQSDPGMLKPRRO-UHFFFAOYSA-N (2-hydroxyphenyl)-[4-(2-methoxyanilino)phenyl]methanone Chemical compound COC1=CC=CC=C1NC1=CC=C(C(=O)C=2C(=CC=CC=2)O)C=C1 VDQSDPGMLKPRRO-UHFFFAOYSA-N 0.000 description 2
- HUEFWHLHDPCOJA-UHFFFAOYSA-N (2-hydroxyphenyl)-[4-(4-methoxyanilino)phenyl]methanone Chemical compound C1=CC(OC)=CC=C1NC1=CC=C(C(=O)C=2C(=CC=CC=2)O)C=C1 HUEFWHLHDPCOJA-UHFFFAOYSA-N 0.000 description 2
- RWXJFXGZWYRWHG-UHFFFAOYSA-N (4-anilinophenyl)-(2-chlorophenyl)methanone Chemical compound ClC1=CC=CC=C1C(=O)C(C=C1)=CC=C1NC1=CC=CC=C1 RWXJFXGZWYRWHG-UHFFFAOYSA-N 0.000 description 2
- FSFMLNLAYYAFPJ-UHFFFAOYSA-N (4-anilinophenyl)-(2-hydroxyphenyl)methanone Chemical compound OC1=CC=CC=C1C(=O)C(C=C1)=CC=C1NC1=CC=CC=C1 FSFMLNLAYYAFPJ-UHFFFAOYSA-N 0.000 description 2
- 125000006526 (C1-C2) alkyl group Chemical group 0.000 description 2
- JAJIPIAHCFBEPI-UHFFFAOYSA-N 9,10-dioxoanthracene-1-sulfonic acid Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2S(=O)(=O)O JAJIPIAHCFBEPI-UHFFFAOYSA-N 0.000 description 2
- 208000030507 AIDS Diseases 0.000 description 2
- 208000002874 Acne Vulgaris Diseases 0.000 description 2
- 206010003645 Atopy Diseases 0.000 description 2
- 0 CC1C=CC(C(c(c(*)c2)ccc2N(*)C2=CC*(C)=CC=C2)=*)=C(*)C=C1 Chemical compound CC1C=CC(C(c(c(*)c2)ccc2N(*)C2=CC*(C)=CC=C2)=*)=C(*)C=C1 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- CAMRNZUAORWZFO-UHFFFAOYSA-N [4-(2-chloroanilino)phenyl]-(2-chlorophenyl)methanone Chemical compound ClC1=CC=CC=C1NC1=CC=C(C(=O)C=2C(=CC=CC=2)Cl)C=C1 CAMRNZUAORWZFO-UHFFFAOYSA-N 0.000 description 2
- QPEFUBQSFHPPLW-UHFFFAOYSA-N [4-(2-hydroxyanilino)phenyl]-(2-hydroxyphenyl)methanone Chemical compound OC1=CC=CC=C1NC1=CC=C(C(=O)C=2C(=CC=CC=2)O)C=C1 QPEFUBQSFHPPLW-UHFFFAOYSA-N 0.000 description 2
- WMLSXLKOFWZQKA-UHFFFAOYSA-N [4-(2-methoxyanilino)phenyl]-(2-methoxyphenyl)methanone Chemical compound COC1=CC=CC=C1NC1=CC=C(C(=O)C=2C(=CC=CC=2)OC)C=C1 WMLSXLKOFWZQKA-UHFFFAOYSA-N 0.000 description 2
- NYHMZFXALPBLMC-UHFFFAOYSA-N [4-(4-hydroxyanilino)phenyl]-(2-hydroxyphenyl)methanone Chemical compound C1=CC(O)=CC=C1NC1=CC=C(C(=O)C=2C(=CC=CC=2)O)C=C1 NYHMZFXALPBLMC-UHFFFAOYSA-N 0.000 description 2
- FAFWTCYMAJSUAP-UHFFFAOYSA-N [4-(4-methoxyanilino)phenyl]-(2-methylphenyl)methanone Chemical compound C1=CC(OC)=CC=C1NC1=CC=C(C(=O)C=2C(=CC=CC=2)C)C=C1 FAFWTCYMAJSUAP-UHFFFAOYSA-N 0.000 description 2
- 206010000496 acne Diseases 0.000 description 2
- 239000000808 adrenergic beta-agonist Substances 0.000 description 2
- 229940125715 antihistaminic agent Drugs 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 150000004492 retinoid derivatives Chemical class 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 2
- 229960001860 salicylate Drugs 0.000 description 2
- NCEXYHBECQHGNR-QZQOTICOSA-N sulfasalazine Chemical compound C1=C(O)C(C(=O)O)=CC(\N=N\C=2C=CC(=CC=2)S(=O)(=O)NC=2N=CC=CC=2)=C1 NCEXYHBECQHGNR-QZQOTICOSA-N 0.000 description 2
- 229960001940 sulfasalazine Drugs 0.000 description 2
- 229940037128 systemic glucocorticoids Drugs 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 229930003231 vitamin Natural products 0.000 description 2
- 239000011782 vitamin Substances 0.000 description 2
- 229940088594 vitamin Drugs 0.000 description 2
- 235000013343 vitamin Nutrition 0.000 description 2
- 150000003722 vitamin derivatives Chemical class 0.000 description 2
- IEPJOHCGXJNNIW-UHFFFAOYSA-N (4-anilino-2-chlorophenyl)-(2-methylphenyl)methanethione Chemical compound CC1=CC=CC=C1C(=S)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1 IEPJOHCGXJNNIW-UHFFFAOYSA-N 0.000 description 1
- VPTQOJQQTLPBGP-UHFFFAOYSA-N (4-anilino-2-chlorophenyl)-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1 VPTQOJQQTLPBGP-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
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 1
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 description 1
- CEJSDKUFKRVDIG-UHFFFAOYSA-N 2-[3-chloro-4-[n-hydroxy-c-(2-methylphenyl)carbonimidoyl]anilino]phenol Chemical compound CC1=CC=CC=C1C(=NO)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1O CEJSDKUFKRVDIG-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
- BVRDQVRQVGRNHG-UHFFFAOYSA-N 2-morpholin-4-ylpyrimido[2,1-a]isoquinolin-4-one Chemical compound N1=C2C3=CC=CC=C3C=CN2C(=O)C=C1N1CCOCC1 BVRDQVRQVGRNHG-UHFFFAOYSA-N 0.000 description 1
- WFOVEDJTASPCIR-UHFFFAOYSA-N 3-[(4-methyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)methylamino]-n-[[2-(trifluoromethyl)phenyl]methyl]benzamide Chemical compound N=1N=C(C=2C=CN=CC=2)N(C)C=1CNC(C=1)=CC=CC=1C(=O)NCC1=CC=CC=C1C(F)(F)F WFOVEDJTASPCIR-UHFFFAOYSA-N 0.000 description 1
- TZZDVPMABRWKIZ-MFTLXVFQSA-N 3-[6-[4-[[1-[4-[(1R,2S)-6-hydroxy-2-phenyl-1,2,3,4-tetrahydronaphthalen-1-yl]phenyl]piperidin-4-yl]methyl]piperazin-1-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound OC=1C=C2CC[C@@H]([C@@H](C2=CC=1)C1=CC=C(C=C1)N1CCC(CC1)CN1CCN(CC1)C=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O)C1=CC=CC=C1 TZZDVPMABRWKIZ-MFTLXVFQSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- OOABJAHWCLGUHQ-UHFFFAOYSA-N 4-[3-chloro-4-(2-methylbenzenecarbothioyl)anilino]-3-methylbenzonitrile Chemical compound CC1=CC(C#N)=CC=C1NC(C=C1Cl)=CC=C1C(=S)C1=CC=CC=C1C OOABJAHWCLGUHQ-UHFFFAOYSA-N 0.000 description 1
- TYUTXGXOAGXOLV-UHFFFAOYSA-N 4-[3-chloro-4-(2-methylbenzoyl)anilino]-3-methylbenzonitrile Chemical compound CC1=CC(C#N)=CC=C1NC(C=C1Cl)=CC=C1C(=O)C1=CC=CC=C1C TYUTXGXOAGXOLV-UHFFFAOYSA-N 0.000 description 1
- FNBNHJJDAXBZQV-UHFFFAOYSA-N 4-[3-chloro-4-[n-hydroxy-c-(2-methylphenyl)carbonimidoyl]anilino]-3-methylbenzonitrile Chemical compound CC1=CC=CC=C1C(=NO)C(C(=C1)Cl)=CC=C1NC1=CC=C(C#N)C=C1C FNBNHJJDAXBZQV-UHFFFAOYSA-N 0.000 description 1
- XWQVQSXLXAXOPJ-QNGMFEMESA-N 4-[[[6-[5-chloro-2-[[4-[[(2r)-1-methoxypropan-2-yl]amino]cyclohexyl]amino]pyridin-4-yl]pyridin-2-yl]amino]methyl]oxane-4-carbonitrile Chemical compound C1CC(N[C@H](C)COC)CCC1NC1=CC(C=2N=C(NCC3(CCOCC3)C#N)C=CC=2)=C(Cl)C=N1 XWQVQSXLXAXOPJ-QNGMFEMESA-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
- YZSCPLGKKMSBMV-UHFFFAOYSA-N 5-fluoro-4-(8-fluoro-4-propan-2-yl-2,3-dihydro-1,4-benzoxazin-6-yl)-N-[5-(1-methylpiperidin-4-yl)pyridin-2-yl]pyrimidin-2-amine Chemical compound FC=1C(=NC(=NC=1)NC1=NC=C(C=C1)C1CCN(CC1)C)C1=CC2=C(OCCN2C(C)C)C(=C1)F YZSCPLGKKMSBMV-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
- 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
- 208000012124 AIDS-related disease 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
- SWALXVDIDHSUNN-UHFFFAOYSA-N C(C)(C)(C)OC1=C(C=CC=C1)NC1=CC(=C(C(C2=C(C=CC=C2)C)=NO)C=C1)Cl Chemical compound C(C)(C)(C)OC1=C(C=CC=C1)NC1=CC(=C(C(C2=C(C=CC=C2)C)=NO)C=C1)Cl SWALXVDIDHSUNN-UHFFFAOYSA-N 0.000 description 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 1
- VZJHQMHIRQTYHC-UHFFFAOYSA-N CC(C=C(C=C1)F)=C1C(C(C=CC=C1NC(C=C2)=C(C)C=C2Br)=C1Cl)=NO Chemical compound CC(C=C(C=C1)F)=C1C(C(C=CC=C1NC(C=C2)=C(C)C=C2Br)=C1Cl)=NO VZJHQMHIRQTYHC-UHFFFAOYSA-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
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- RAPBNVDSDCTNRC-UHFFFAOYSA-N Chlorobenzilate Chemical compound C=1C=C(Cl)C=CC=1C(O)(C(=O)OCC)C1=CC=C(Cl)C=C1 RAPBNVDSDCTNRC-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- CLCTZVRHDOAUGJ-UHFFFAOYSA-N N-[4-(3-chloro-4-cyanophenoxy)cyclohexyl]-6-[4-[[4-[2-(2,6-dioxopiperidin-3-yl)-6-fluoro-1,3-dioxoisoindol-5-yl]piperazin-1-yl]methyl]piperidin-1-yl]pyridazine-3-carboxamide Chemical compound FC1=CC2=C(C=C1N1CCN(CC3CCN(CC3)C3=CC=C(N=N3)C(=O)NC3CCC(CC3)OC3=CC(Cl)=C(C=C3)C#N)CC1)C(=O)N(C1CCC(=O)NC1=O)C2=O CLCTZVRHDOAUGJ-UHFFFAOYSA-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
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 208000001132 Osteoporosis Diseases 0.000 description 1
- 241001131927 Placea Species 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- GUGOEEXESWIERI-UHFFFAOYSA-N Terfenadine Chemical compound C1=CC(C(C)(C)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 GUGOEEXESWIERI-UHFFFAOYSA-N 0.000 description 1
- 229930003316 Vitamin D Natural products 0.000 description 1
- QYSXJUFSXHHAJI-XFEUOLMDSA-N Vitamin D3 Natural products C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CCCC(C)C)=C/C=C1\C[C@@H](O)CCC1=C QYSXJUFSXHHAJI-XFEUOLMDSA-N 0.000 description 1
- DITQJEPKOBXFKT-UHFFFAOYSA-N [2-chloro-4-(2-chloroanilino)phenyl]-(2-methylphenyl)methanethione Chemical compound CC1=CC=CC=C1C(=S)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1Cl DITQJEPKOBXFKT-UHFFFAOYSA-N 0.000 description 1
- FHPLTNWXKTYPLN-UHFFFAOYSA-N [2-chloro-4-(2-chloroanilino)phenyl]-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1Cl FHPLTNWXKTYPLN-UHFFFAOYSA-N 0.000 description 1
- AGNKLBSJKAXDTF-UHFFFAOYSA-N [2-chloro-4-(2-ethylanilino)phenyl]-(2-methylphenyl)methanethione Chemical compound CCC1=CC=CC=C1NC(C=C1Cl)=CC=C1C(=S)C1=CC=CC=C1C AGNKLBSJKAXDTF-UHFFFAOYSA-N 0.000 description 1
- CBPQSDOAHLITKP-UHFFFAOYSA-N [2-chloro-4-(2-ethylanilino)phenyl]-(2-methylphenyl)methanone Chemical compound CCC1=CC=CC=C1NC(C=C1Cl)=CC=C1C(=O)C1=CC=CC=C1C CBPQSDOAHLITKP-UHFFFAOYSA-N 0.000 description 1
- KSRAQZGVVKYHMT-UHFFFAOYSA-N [2-chloro-4-(2-fluoroanilino)phenyl]-(2-methylphenyl)methanethione Chemical compound CC1=CC=CC=C1C(=S)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1F KSRAQZGVVKYHMT-UHFFFAOYSA-N 0.000 description 1
- AKGXLYCPRQHBRS-UHFFFAOYSA-N [2-chloro-4-(2-fluoroanilino)phenyl]-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1F AKGXLYCPRQHBRS-UHFFFAOYSA-N 0.000 description 1
- BWHAJDWYLONQOE-UHFFFAOYSA-N [2-chloro-4-(2-hydroxyanilino)phenyl]-(2-methylphenyl)methanethione Chemical compound CC1=CC=CC=C1C(=S)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1O BWHAJDWYLONQOE-UHFFFAOYSA-N 0.000 description 1
- IKQXPVMJCWBISC-UHFFFAOYSA-N [2-chloro-4-(2-hydroxyanilino)phenyl]-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1O IKQXPVMJCWBISC-UHFFFAOYSA-N 0.000 description 1
- XAKPIMXCACWMJQ-UHFFFAOYSA-N [2-chloro-4-(2-methoxyanilino)phenyl]-(2-methylphenyl)methanethione Chemical compound COC1=CC=CC=C1NC(C=C1Cl)=CC=C1C(=S)C1=CC=CC=C1C XAKPIMXCACWMJQ-UHFFFAOYSA-N 0.000 description 1
- FBIZHLQOMDXRCU-UHFFFAOYSA-N [2-chloro-4-(2-methoxyanilino)phenyl]-(2-methylphenyl)methanone Chemical compound COC1=CC=CC=C1NC(C=C1Cl)=CC=C1C(=O)C1=CC=CC=C1C FBIZHLQOMDXRCU-UHFFFAOYSA-N 0.000 description 1
- RUACGBIFQYPTCA-UHFFFAOYSA-N [2-chloro-4-(2-methylanilino)phenyl]-(2-methylphenyl)methanethione Chemical compound CC1=CC=CC=C1NC(C=C1Cl)=CC=C1C(=S)C1=CC=CC=C1C RUACGBIFQYPTCA-UHFFFAOYSA-N 0.000 description 1
- LUZARSGELRSGPD-UHFFFAOYSA-N [2-chloro-4-(2-methylanilino)phenyl]-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1NC(C=C1Cl)=CC=C1C(=O)C1=CC=CC=C1C LUZARSGELRSGPD-UHFFFAOYSA-N 0.000 description 1
- KZFPDEBCGCSIIM-UHFFFAOYSA-N [2-chloro-4-(2-phenylanilino)phenyl]-(2-methylphenyl)methanethione Chemical compound CC1=CC=CC=C1C(=S)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1C1=CC=CC=C1 KZFPDEBCGCSIIM-UHFFFAOYSA-N 0.000 description 1
- YNALKNHADYCHJN-UHFFFAOYSA-N [2-chloro-4-(2-phenylanilino)phenyl]-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1C1=CC=CC=C1 YNALKNHADYCHJN-UHFFFAOYSA-N 0.000 description 1
- AWNCHQBXHRJGBD-UHFFFAOYSA-N [2-chloro-4-(3,4-difluoroanilino)phenyl]-(2-methylphenyl)methanethione Chemical compound CC1=CC=CC=C1C(=S)C(C(=C1)Cl)=CC=C1NC1=CC=C(F)C(F)=C1 AWNCHQBXHRJGBD-UHFFFAOYSA-N 0.000 description 1
- IRPXCVLNJJICSZ-UHFFFAOYSA-N [2-chloro-4-(3,4-difluoroanilino)phenyl]-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=C(F)C(F)=C1 IRPXCVLNJJICSZ-UHFFFAOYSA-N 0.000 description 1
- CXUNGOJKRUFSBZ-UHFFFAOYSA-N [2-chloro-4-(3,5-difluoroanilino)phenyl]-(2-methylphenyl)methanethione Chemical compound CC1=CC=CC=C1C(=S)C(C(=C1)Cl)=CC=C1NC1=CC(F)=CC(F)=C1 CXUNGOJKRUFSBZ-UHFFFAOYSA-N 0.000 description 1
- PGWCJRFNRFYNQQ-UHFFFAOYSA-N [2-chloro-4-(3,5-difluoroanilino)phenyl]-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC(F)=CC(F)=C1 PGWCJRFNRFYNQQ-UHFFFAOYSA-N 0.000 description 1
- KDLMVHFXUISMJY-UHFFFAOYSA-N [2-chloro-4-(3-chloroanilino)phenyl]-(2-methylphenyl)methanethione Chemical compound CC1=CC=CC=C1C(=S)C(C(=C1)Cl)=CC=C1NC1=CC=CC(Cl)=C1 KDLMVHFXUISMJY-UHFFFAOYSA-N 0.000 description 1
- ZZJCFYROROWZKV-UHFFFAOYSA-N [2-chloro-4-(3-chloroanilino)phenyl]-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC(Cl)=C1 ZZJCFYROROWZKV-UHFFFAOYSA-N 0.000 description 1
- GAGLSFUHGWCYQN-UHFFFAOYSA-N [2-chloro-4-(3-fluoro-2-methylanilino)phenyl]-(2-methylphenyl)methanethione Chemical compound CC1=CC=CC=C1C(=S)C(C(=C1)Cl)=CC=C1NC1=CC=CC(F)=C1C GAGLSFUHGWCYQN-UHFFFAOYSA-N 0.000 description 1
- ICGCZHMRFLVOIF-UHFFFAOYSA-N [2-chloro-4-(3-fluoro-2-methylanilino)phenyl]-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC(F)=C1C ICGCZHMRFLVOIF-UHFFFAOYSA-N 0.000 description 1
- KBZOACWWUYEEQT-UHFFFAOYSA-N [2-chloro-4-(3-fluoroanilino)phenyl]-(2-methylphenyl)methanethione Chemical compound CC1=CC=CC=C1C(=S)C(C(=C1)Cl)=CC=C1NC1=CC=CC(F)=C1 KBZOACWWUYEEQT-UHFFFAOYSA-N 0.000 description 1
- JTQNHKWZNCAJLV-UHFFFAOYSA-N [2-chloro-4-(3-fluoroanilino)phenyl]-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC(F)=C1 JTQNHKWZNCAJLV-UHFFFAOYSA-N 0.000 description 1
- LOOQGJFFSQQGDA-UHFFFAOYSA-N [2-chloro-4-(3-methoxyanilino)phenyl]-(2-methylphenyl)methanethione Chemical compound COC1=CC=CC(NC=2C=C(Cl)C(C(=S)C=3C(=CC=CC=3)C)=CC=2)=C1 LOOQGJFFSQQGDA-UHFFFAOYSA-N 0.000 description 1
- KFYGULIWHQWXKE-UHFFFAOYSA-N [2-chloro-4-(3-methoxyanilino)phenyl]-(2-methylphenyl)methanone Chemical compound COC1=CC=CC(NC=2C=C(Cl)C(C(=O)C=3C(=CC=CC=3)C)=CC=2)=C1 KFYGULIWHQWXKE-UHFFFAOYSA-N 0.000 description 1
- DQDAYKOCZZKIMJ-UHFFFAOYSA-N [2-chloro-4-(3-methylanilino)phenyl]-(2-methylphenyl)methanethione Chemical compound CC1=CC=CC(NC=2C=C(Cl)C(C(=S)C=3C(=CC=CC=3)C)=CC=2)=C1 DQDAYKOCZZKIMJ-UHFFFAOYSA-N 0.000 description 1
- VVKYWOOQDLYVMB-UHFFFAOYSA-N [2-chloro-4-(3-methylanilino)phenyl]-(2-methylphenyl)methanone Chemical compound CC1=CC=CC(NC=2C=C(Cl)C(C(=O)C=3C(=CC=CC=3)C)=CC=2)=C1 VVKYWOOQDLYVMB-UHFFFAOYSA-N 0.000 description 1
- SUJSMCXKSVFHSN-UHFFFAOYSA-N [2-chloro-4-(3-phenylanilino)phenyl]-(2-methylphenyl)methanethione Chemical compound CC1=CC=CC=C1C(=S)C(C(=C1)Cl)=CC=C1NC1=CC=CC(C=2C=CC=CC=2)=C1 SUJSMCXKSVFHSN-UHFFFAOYSA-N 0.000 description 1
- XHOKVTACRDQJBF-UHFFFAOYSA-N [2-chloro-4-(3-phenylanilino)phenyl]-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC(C=2C=CC=CC=2)=C1 XHOKVTACRDQJBF-UHFFFAOYSA-N 0.000 description 1
- BUOQBXYMEXMPJR-UHFFFAOYSA-N [2-chloro-4-(4-chloro-2-methylanilino)phenyl]-(2-methylphenyl)methanethione Chemical compound CC1=CC=CC=C1C(=S)C(C(=C1)Cl)=CC=C1NC1=CC=C(Cl)C=C1C BUOQBXYMEXMPJR-UHFFFAOYSA-N 0.000 description 1
- VSZSQBMEARYCGR-UHFFFAOYSA-N [2-chloro-4-(4-chloro-2-methylanilino)phenyl]-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=C(Cl)C=C1C VSZSQBMEARYCGR-UHFFFAOYSA-N 0.000 description 1
- ASUADGYENUDEQH-UHFFFAOYSA-N [2-chloro-4-(4-chloro-3-fluoroanilino)phenyl]-(2-methylphenyl)methanethione Chemical compound CC1=CC=CC=C1C(=S)C(C(=C1)Cl)=CC=C1NC1=CC=C(Cl)C(F)=C1 ASUADGYENUDEQH-UHFFFAOYSA-N 0.000 description 1
- JBRGDIGMNOKGMI-UHFFFAOYSA-N [2-chloro-4-(4-chloro-3-fluoroanilino)phenyl]-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=C(Cl)C(F)=C1 JBRGDIGMNOKGMI-UHFFFAOYSA-N 0.000 description 1
- BNBUVVRVTZUQNZ-UHFFFAOYSA-N [2-chloro-4-(4-chloroanilino)phenyl]-(2-methylphenyl)methanethione Chemical compound CC1=CC=CC=C1C(=S)C(C(=C1)Cl)=CC=C1NC1=CC=C(Cl)C=C1 BNBUVVRVTZUQNZ-UHFFFAOYSA-N 0.000 description 1
- KUOWVCASQRQZRZ-UHFFFAOYSA-N [2-chloro-4-(4-chloroanilino)phenyl]-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=C(Cl)C=C1 KUOWVCASQRQZRZ-UHFFFAOYSA-N 0.000 description 1
- JAOKEHIGERXMER-UHFFFAOYSA-N [2-chloro-4-(4-fluoro-2-methylanilino)phenyl]-(2-methylphenyl)methanethione Chemical compound CC1=CC=CC=C1C(=S)C(C(=C1)Cl)=CC=C1NC1=CC=C(F)C=C1C JAOKEHIGERXMER-UHFFFAOYSA-N 0.000 description 1
- QIBLVZMAUUVSMB-UHFFFAOYSA-N [2-chloro-4-(4-fluoro-2-methylanilino)phenyl]-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=C(F)C=C1C QIBLVZMAUUVSMB-UHFFFAOYSA-N 0.000 description 1
- GRCWLCUDIJTHRG-UHFFFAOYSA-N [2-chloro-4-(4-fluoro-2-methylanilino)phenyl]-(3-fluoro-2-methylphenyl)methanethione Chemical compound CC1=CC(F)=CC=C1NC(C=C1Cl)=CC=C1C(=S)C1=CC=CC(F)=C1C GRCWLCUDIJTHRG-UHFFFAOYSA-N 0.000 description 1
- YEGOSPBDGNVMFW-UHFFFAOYSA-N [2-chloro-4-(4-fluoro-2-methylanilino)phenyl]-(3-fluoro-2-methylphenyl)methanone Chemical compound CC1=CC(F)=CC=C1NC(C=C1Cl)=CC=C1C(=O)C1=CC=CC(F)=C1C YEGOSPBDGNVMFW-UHFFFAOYSA-N 0.000 description 1
- KQSCPJWHQGTTSN-UHFFFAOYSA-N [2-chloro-4-(4-fluoro-n,2-dimethylanilino)phenyl]-(2-methylphenyl)methanethione Chemical compound C=1C=C(F)C=C(C)C=1N(C)C(C=C1Cl)=CC=C1C(=S)C1=CC=CC=C1C KQSCPJWHQGTTSN-UHFFFAOYSA-N 0.000 description 1
- FXINJXGELVRRDI-UHFFFAOYSA-N [2-chloro-4-(4-fluoro-n,2-dimethylanilino)phenyl]-(2-methylphenyl)methanone Chemical compound C=1C=C(F)C=C(C)C=1N(C)C(C=C1Cl)=CC=C1C(=O)C1=CC=CC=C1C FXINJXGELVRRDI-UHFFFAOYSA-N 0.000 description 1
- YTACGIBAEWNYHB-UHFFFAOYSA-N [2-chloro-4-(4-phenylanilino)phenyl]-(2-methylphenyl)methanethione Chemical compound CC1=CC=CC=C1C(=S)C(C(=C1)Cl)=CC=C1NC1=CC=C(C=2C=CC=CC=2)C=C1 YTACGIBAEWNYHB-UHFFFAOYSA-N 0.000 description 1
- DDQXYZCPHQZFQW-UHFFFAOYSA-N [2-chloro-4-(4-phenylanilino)phenyl]-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=C(C=2C=CC=CC=2)C=C1 DDQXYZCPHQZFQW-UHFFFAOYSA-N 0.000 description 1
- SUHBYJFACRZIGB-UHFFFAOYSA-N [2-chloro-4-(5-fluoro-2-methylanilino)phenyl]-(2-methylphenyl)methanethione Chemical compound CC1=CC=C(F)C=C1NC(C=C1Cl)=CC=C1C(=S)C1=CC=CC=C1C SUHBYJFACRZIGB-UHFFFAOYSA-N 0.000 description 1
- PXFJYHUBEMGRLD-UHFFFAOYSA-N [2-chloro-4-(5-fluoro-2-methylanilino)phenyl]-(2-methylphenyl)methanone Chemical compound CC1=CC=C(F)C=C1NC(C=C1Cl)=CC=C1C(=O)C1=CC=CC=C1C PXFJYHUBEMGRLD-UHFFFAOYSA-N 0.000 description 1
- GRWLQZVMTNOILJ-UHFFFAOYSA-N [2-chloro-4-[2-(trifluoromethyl)anilino]phenyl]-(2-methylphenyl)methanethione Chemical compound CC1=CC=CC=C1C(=S)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1C(F)(F)F GRWLQZVMTNOILJ-UHFFFAOYSA-N 0.000 description 1
- MXKZCXJRQPPBHM-UHFFFAOYSA-N [2-chloro-4-[2-(trifluoromethyl)anilino]phenyl]-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1C(F)(F)F MXKZCXJRQPPBHM-UHFFFAOYSA-N 0.000 description 1
- PJDQOAOWJKRUQC-UHFFFAOYSA-N [2-chloro-4-[2-[(2-methylpropan-2-yl)oxy]anilino]phenyl]-(2-methylphenyl)methanethione Chemical compound CC1=CC=CC=C1C(=S)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1OC(C)(C)C PJDQOAOWJKRUQC-UHFFFAOYSA-N 0.000 description 1
- NLQFXFHDJLFAOW-UHFFFAOYSA-N [2-chloro-4-[2-[(2-methylpropan-2-yl)oxy]anilino]phenyl]-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1OC(C)(C)C NLQFXFHDJLFAOW-UHFFFAOYSA-N 0.000 description 1
- GHEPKVKJNYDYQW-UHFFFAOYSA-N [2-chloro-4-[3-(trifluoromethyl)anilino]phenyl]-(2-methylphenyl)methanethione Chemical compound CC1=CC=CC=C1C(=S)C(C(=C1)Cl)=CC=C1NC1=CC=CC(C(F)(F)F)=C1 GHEPKVKJNYDYQW-UHFFFAOYSA-N 0.000 description 1
- WTEKRXGIOVGHQH-UHFFFAOYSA-N [2-chloro-4-[3-(trifluoromethyl)anilino]phenyl]-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC(C(F)(F)F)=C1 WTEKRXGIOVGHQH-UHFFFAOYSA-N 0.000 description 1
- NTDZDBZYKXDWIU-UHFFFAOYSA-N [4-(2-bromoanilino)-2-chlorophenyl]-(2-methylphenyl)methanethione Chemical compound CC1=CC=CC=C1C(=S)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1Br NTDZDBZYKXDWIU-UHFFFAOYSA-N 0.000 description 1
- YXXCMERBQVUIOF-UHFFFAOYSA-N [4-(2-bromoanilino)-2-chlorophenyl]-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1Br YXXCMERBQVUIOF-UHFFFAOYSA-N 0.000 description 1
- VTTMGLUEJXDBAS-UHFFFAOYSA-N [4-(3-bromoanilino)-2-chlorophenyl]-(2-methylphenyl)methanethione Chemical compound CC1=CC=CC=C1C(=S)C(C(=C1)Cl)=CC=C1NC1=CC=CC(Br)=C1 VTTMGLUEJXDBAS-UHFFFAOYSA-N 0.000 description 1
- VWBDBNBTNHIIDE-UHFFFAOYSA-N [4-(3-bromoanilino)-2-chlorophenyl]-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC(Br)=C1 VWBDBNBTNHIIDE-UHFFFAOYSA-N 0.000 description 1
- UWQXHMDMINWIST-UHFFFAOYSA-N [4-(4-bromo-2,5-difluoroanilino)-2-chlorophenyl]-(2-methylphenyl)methanethione Chemical compound CC1=CC=CC=C1C(=S)C(C(=C1)Cl)=CC=C1NC1=CC(F)=C(Br)C=C1F UWQXHMDMINWIST-UHFFFAOYSA-N 0.000 description 1
- LKYTVZHTKHVYOS-UHFFFAOYSA-N [4-(4-bromo-2,5-difluoroanilino)-2-chlorophenyl]-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC(F)=C(Br)C=C1F LKYTVZHTKHVYOS-UHFFFAOYSA-N 0.000 description 1
- VVMGZRKLFWVPSV-UHFFFAOYSA-N [4-(4-bromo-2-chloroanilino)-2-chlorophenyl]-(2-methylphenyl)methanethione Chemical compound CC1=CC=CC=C1C(=S)C(C(=C1)Cl)=CC=C1NC1=CC=C(Br)C=C1Cl VVMGZRKLFWVPSV-UHFFFAOYSA-N 0.000 description 1
- ODLGKXXSBNIUER-UHFFFAOYSA-N [4-(4-bromo-2-chloroanilino)-2-chlorophenyl]-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=C(Br)C=C1Cl ODLGKXXSBNIUER-UHFFFAOYSA-N 0.000 description 1
- ZYSQTALRAZSPHR-UHFFFAOYSA-N [4-(4-bromo-2-methylanilino)-2-chlorophenyl]-(2,5-dimethylphenyl)methanethione Chemical compound CC1=CC=C(C)C(C(=S)C=2C(=CC(NC=3C(=CC(Br)=CC=3)C)=CC=2)Cl)=C1 ZYSQTALRAZSPHR-UHFFFAOYSA-N 0.000 description 1
- QJLBTRHUTJJCSW-UHFFFAOYSA-N [4-(4-bromo-2-methylanilino)-2-chlorophenyl]-(2,5-dimethylphenyl)methanone Chemical compound CC1=CC=C(C)C(C(=O)C=2C(=CC(NC=3C(=CC(Br)=CC=3)C)=CC=2)Cl)=C1 QJLBTRHUTJJCSW-UHFFFAOYSA-N 0.000 description 1
- TUTWGPISUQGKBD-UHFFFAOYSA-N [4-(4-bromo-2-methylanilino)-2-chlorophenyl]-(2-methylphenyl)methanethione Chemical compound CC1=CC=CC=C1C(=S)C(C(=C1)Cl)=CC=C1NC1=CC=C(Br)C=C1C TUTWGPISUQGKBD-UHFFFAOYSA-N 0.000 description 1
- SMHGTACFCJULBI-UHFFFAOYSA-N [4-(4-bromo-2-methylanilino)-2-chlorophenyl]-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=C(Br)C=C1C SMHGTACFCJULBI-UHFFFAOYSA-N 0.000 description 1
- JSOANEOXPZUNBP-UHFFFAOYSA-N [4-(4-bromo-2-methylanilino)-2-chlorophenyl]-(3-chloro-2-methylphenyl)methanethione Chemical compound CC1=CC(Br)=CC=C1NC(C=C1Cl)=CC=C1C(=S)C1=CC=CC(Cl)=C1C JSOANEOXPZUNBP-UHFFFAOYSA-N 0.000 description 1
- UTVAJFWUMZRJPC-UHFFFAOYSA-N [4-(4-bromo-2-methylanilino)-2-chlorophenyl]-(3-chloro-2-methylphenyl)methanone Chemical compound CC1=CC(Br)=CC=C1NC(C=C1Cl)=CC=C1C(=O)C1=CC=CC(Cl)=C1C UTVAJFWUMZRJPC-UHFFFAOYSA-N 0.000 description 1
- FXKBJMRILKYXOH-UHFFFAOYSA-N [4-(4-bromo-2-methylanilino)-2-chlorophenyl]-(4-chloro-2-methylphenyl)methanethione Chemical compound CC1=CC(Br)=CC=C1NC(C=C1Cl)=CC=C1C(=S)C1=CC=C(Cl)C=C1C FXKBJMRILKYXOH-UHFFFAOYSA-N 0.000 description 1
- SPZPHOSFAQIWDL-UHFFFAOYSA-N [4-(4-bromo-2-methylanilino)-2-chlorophenyl]-(4-chloro-2-methylphenyl)methanone Chemical compound CC1=CC(Br)=CC=C1NC(C=C1Cl)=CC=C1C(=O)C1=CC=C(Cl)C=C1C SPZPHOSFAQIWDL-UHFFFAOYSA-N 0.000 description 1
- RAAWZLKQTYMCAS-UHFFFAOYSA-N [4-(4-bromo-2-methylanilino)-2-chlorophenyl]-(4-ethoxy-2-methylphenyl)methanone Chemical compound CC1=CC(OCC)=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=C(Br)C=C1C RAAWZLKQTYMCAS-UHFFFAOYSA-N 0.000 description 1
- TYKRTEOOAZKHKQ-UHFFFAOYSA-N [4-(4-bromo-2-methylanilino)-2-chlorophenyl]-(4-fluoro-2-methylphenyl)methanone Chemical compound CC1=CC(Br)=CC=C1NC(C=C1Cl)=CC=C1C(=O)C1=CC=C(F)C=C1C TYKRTEOOAZKHKQ-UHFFFAOYSA-N 0.000 description 1
- PRVQTNISPQNOFF-UHFFFAOYSA-N [4-(4-bromo-2-methylanilino)-2-chlorophenyl]-(4-methoxy-2-methylphenyl)methanethione Chemical compound CC1=CC(OC)=CC=C1C(=S)C(C(=C1)Cl)=CC=C1NC1=CC=C(Br)C=C1C PRVQTNISPQNOFF-UHFFFAOYSA-N 0.000 description 1
- BUMZTXNVVXTXOK-UHFFFAOYSA-N [4-(4-bromo-2-methylanilino)-2-chlorophenyl]-(4-methoxy-2-methylphenyl)methanone Chemical compound CC1=CC(OC)=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=C(Br)C=C1C BUMZTXNVVXTXOK-UHFFFAOYSA-N 0.000 description 1
- RFGQUZJHDYUMLE-UHFFFAOYSA-N [4-(4-bromo-2-methylanilino)-2-fluorophenyl]-(2-methylphenyl)methanethione Chemical compound CC1=CC=CC=C1C(=S)C(C(=C1)F)=CC=C1NC1=CC=C(Br)C=C1C RFGQUZJHDYUMLE-UHFFFAOYSA-N 0.000 description 1
- BEUJIHNUXZAVQD-UHFFFAOYSA-N [4-(4-bromo-2-methylanilino)-2-fluorophenyl]-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)F)=CC=C1NC1=CC=C(Br)C=C1C BEUJIHNUXZAVQD-UHFFFAOYSA-N 0.000 description 1
- YEMFHZNAYWMFSX-UHFFFAOYSA-N [4-(4-bromo-2-methylanilino)phenyl]-[4-(2-chloroethoxy)-2-methylphenyl]methanethione Chemical compound CC1=CC(Br)=CC=C1NC1=CC=C(C(=S)C=2C(=CC(OCCCl)=CC=2)C)C=C1 YEMFHZNAYWMFSX-UHFFFAOYSA-N 0.000 description 1
- RNFDILQWXSGJNV-UHFFFAOYSA-N [4-(4-bromo-3-fluoroanilino)-2-chlorophenyl]-(2-methylphenyl)methanethione Chemical compound CC1=CC=CC=C1C(=S)C(C(=C1)Cl)=CC=C1NC1=CC=C(Br)C(F)=C1 RNFDILQWXSGJNV-UHFFFAOYSA-N 0.000 description 1
- GCSXQEKWZAIUNS-UHFFFAOYSA-N [4-(4-bromo-3-fluoroanilino)-2-chlorophenyl]-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=C(Br)C(F)=C1 GCSXQEKWZAIUNS-UHFFFAOYSA-N 0.000 description 1
- MLDUYDROLDIYQY-UHFFFAOYSA-N [4-(4-bromo-n-ethyl-2-methylanilino)-2-chlorophenyl]-(2-methylphenyl)methanethione Chemical compound C=1C=C(Br)C=C(C)C=1N(CC)C(C=C1Cl)=CC=C1C(=S)C1=CC=CC=C1C MLDUYDROLDIYQY-UHFFFAOYSA-N 0.000 description 1
- SUAZGAULEMZNEO-UHFFFAOYSA-N [4-(4-bromo-n-ethyl-2-methylanilino)-2-chlorophenyl]-(2-methylphenyl)methanone Chemical compound C=1C=C(Br)C=C(C)C=1N(CC)C(C=C1Cl)=CC=C1C(=O)C1=CC=CC=C1C SUAZGAULEMZNEO-UHFFFAOYSA-N 0.000 description 1
- JOZGMYXHKVZYPF-UHFFFAOYSA-N [4-(4-bromoanilino)-2-chlorophenyl]-(2-methylphenyl)methanethione Chemical compound CC1=CC=CC=C1C(=S)C(C(=C1)Cl)=CC=C1NC1=CC=C(Br)C=C1 JOZGMYXHKVZYPF-UHFFFAOYSA-N 0.000 description 1
- NHDUNYNBPYSAGE-UHFFFAOYSA-N [4-(4-bromoanilino)-2-chlorophenyl]-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=C(Br)C=C1 NHDUNYNBPYSAGE-UHFFFAOYSA-N 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 239000000048 adrenergic agonist 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
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000001387 anti-histamine Effects 0.000 description 1
- 125000001246 bromo group Chemical group Br* 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
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 229940111134 coxibs Drugs 0.000 description 1
- 239000003255 cyclooxygenase 2 inhibitor Substances 0.000 description 1
- BFXLJWUGRPGMFU-UHFFFAOYSA-N dipropoxyphosphinothioyl n,n-diethylcarbamodithioate;sulfane Chemical compound S.CCCOP(=S)(OCCC)SC(=S)N(CC)CC BFXLJWUGRPGMFU-UHFFFAOYSA-N 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 150000002343 gold Chemical class 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229940071870 hydroiodic acid Drugs 0.000 description 1
- 208000027866 inflammatory disease Diseases 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- GXFQZHNSSKYZBZ-UHFFFAOYSA-N n-[(4-anilino-2-chlorophenyl)-(2-methylphenyl)methylidene]hydroxylamine Chemical compound CC1=CC=CC=C1C(=NO)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1 GXFQZHNSSKYZBZ-UHFFFAOYSA-N 0.000 description 1
- ZVXMXTDOPGYCIE-UHFFFAOYSA-N n-[[2-chloro-4-(2-chloroanilino)phenyl]-(2-methylphenyl)methylidene]hydroxylamine Chemical compound CC1=CC=CC=C1C(=NO)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1Cl ZVXMXTDOPGYCIE-UHFFFAOYSA-N 0.000 description 1
- VQTONSSAHCBHFG-UHFFFAOYSA-N n-[[2-chloro-4-(2-ethylanilino)phenyl]-(2-methylphenyl)methylidene]hydroxylamine Chemical compound CCC1=CC=CC=C1NC(C=C1Cl)=CC=C1C(=NO)C1=CC=CC=C1C VQTONSSAHCBHFG-UHFFFAOYSA-N 0.000 description 1
- HOQQGHDEGZEBDU-UHFFFAOYSA-N n-[[2-chloro-4-(2-fluoroanilino)phenyl]-(2-methylphenyl)methylidene]hydroxylamine Chemical compound CC1=CC=CC=C1C(=NO)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1F HOQQGHDEGZEBDU-UHFFFAOYSA-N 0.000 description 1
- ATNBRHVFPWQJTC-UHFFFAOYSA-N n-[[2-chloro-4-(2-methoxyanilino)phenyl]-(2-methylphenyl)methylidene]hydroxylamine Chemical compound COC1=CC=CC=C1NC(C=C1Cl)=CC=C1C(=NO)C1=CC=CC=C1C ATNBRHVFPWQJTC-UHFFFAOYSA-N 0.000 description 1
- GBRSXNRFIDZWNE-UHFFFAOYSA-N n-[[2-chloro-4-(2-methylanilino)phenyl]-(2-methylphenyl)methylidene]hydroxylamine Chemical compound CC1=CC=CC=C1NC(C=C1Cl)=CC=C1C(=NO)C1=CC=CC=C1C GBRSXNRFIDZWNE-UHFFFAOYSA-N 0.000 description 1
- YCWTYTDEBDXULL-UHFFFAOYSA-N n-[[2-chloro-4-(2-phenylanilino)phenyl]-(2-methylphenyl)methylidene]hydroxylamine Chemical compound CC1=CC=CC=C1C(=NO)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1C1=CC=CC=C1 YCWTYTDEBDXULL-UHFFFAOYSA-N 0.000 description 1
- OXBWVRJSTRPRFJ-UHFFFAOYSA-N n-[[2-chloro-4-(3,4-difluoroanilino)phenyl]-(2-methylphenyl)methylidene]hydroxylamine Chemical compound CC1=CC=CC=C1C(=NO)C(C(=C1)Cl)=CC=C1NC1=CC=C(F)C(F)=C1 OXBWVRJSTRPRFJ-UHFFFAOYSA-N 0.000 description 1
- DQEYXKPNCYYTET-UHFFFAOYSA-N n-[[2-chloro-4-(3,5-difluoroanilino)phenyl]-(2-methylphenyl)methylidene]hydroxylamine Chemical compound CC1=CC=CC=C1C(=NO)C(C(=C1)Cl)=CC=C1NC1=CC(F)=CC(F)=C1 DQEYXKPNCYYTET-UHFFFAOYSA-N 0.000 description 1
- CDRVNFITGRDLCU-UHFFFAOYSA-N n-[[2-chloro-4-(3-chloroanilino)phenyl]-(2-methylphenyl)methylidene]hydroxylamine Chemical compound CC1=CC=CC=C1C(=NO)C(C(=C1)Cl)=CC=C1NC1=CC=CC(Cl)=C1 CDRVNFITGRDLCU-UHFFFAOYSA-N 0.000 description 1
- RTRKSKMWBMVDLC-UHFFFAOYSA-N n-[[2-chloro-4-(3-fluoro-2-methylanilino)phenyl]-(2-methylphenyl)methylidene]hydroxylamine Chemical compound CC1=CC=CC=C1C(=NO)C(C(=C1)Cl)=CC=C1NC1=CC=CC(F)=C1C RTRKSKMWBMVDLC-UHFFFAOYSA-N 0.000 description 1
- HPVFLZDGQRVAKT-UHFFFAOYSA-N n-[[2-chloro-4-(3-fluoroanilino)phenyl]-(2-methylphenyl)methylidene]hydroxylamine Chemical compound CC1=CC=CC=C1C(=NO)C(C(=C1)Cl)=CC=C1NC1=CC=CC(F)=C1 HPVFLZDGQRVAKT-UHFFFAOYSA-N 0.000 description 1
- XQPNOYSOZYFANY-UHFFFAOYSA-N n-[[2-chloro-4-(3-methoxyanilino)phenyl]-(2-methylphenyl)methylidene]hydroxylamine Chemical compound COC1=CC=CC(NC=2C=C(Cl)C(C(=NO)C=3C(=CC=CC=3)C)=CC=2)=C1 XQPNOYSOZYFANY-UHFFFAOYSA-N 0.000 description 1
- MRLMQAHBNMMECJ-UHFFFAOYSA-N n-[[2-chloro-4-(3-methylanilino)phenyl]-(2-methylphenyl)methylidene]hydroxylamine Chemical compound CC1=CC=CC(NC=2C=C(Cl)C(C(=NO)C=3C(=CC=CC=3)C)=CC=2)=C1 MRLMQAHBNMMECJ-UHFFFAOYSA-N 0.000 description 1
- MFUNDMMBSJZCQP-UHFFFAOYSA-N n-[[2-chloro-4-(3-phenylanilino)phenyl]-(2-methylphenyl)methylidene]hydroxylamine Chemical compound CC1=CC=CC=C1C(=NO)C(C(=C1)Cl)=CC=C1NC1=CC=CC(C=2C=CC=CC=2)=C1 MFUNDMMBSJZCQP-UHFFFAOYSA-N 0.000 description 1
- YXHVKEPEDDODCL-UHFFFAOYSA-N n-[[2-chloro-4-(4-chloro-2-methylanilino)phenyl]-(2-methylphenyl)methylidene]hydroxylamine Chemical compound CC1=CC=CC=C1C(=NO)C(C(=C1)Cl)=CC=C1NC1=CC=C(Cl)C=C1C YXHVKEPEDDODCL-UHFFFAOYSA-N 0.000 description 1
- PGICSXWOAPBUQU-UHFFFAOYSA-N n-[[2-chloro-4-(4-chloro-3-fluoroanilino)phenyl]-(2-methylphenyl)methylidene]hydroxylamine Chemical compound CC1=CC=CC=C1C(=NO)C(C(=C1)Cl)=CC=C1NC1=CC=C(Cl)C(F)=C1 PGICSXWOAPBUQU-UHFFFAOYSA-N 0.000 description 1
- NZNMZWCDKXHMJH-UHFFFAOYSA-N n-[[2-chloro-4-(4-chloroanilino)phenyl]-(2-methylphenyl)methylidene]hydroxylamine Chemical compound CC1=CC=CC=C1C(=NO)C(C(=C1)Cl)=CC=C1NC1=CC=C(Cl)C=C1 NZNMZWCDKXHMJH-UHFFFAOYSA-N 0.000 description 1
- VSCOXSDWLIBETA-UHFFFAOYSA-N n-[[2-chloro-4-(4-fluoro-2-methylanilino)phenyl]-(2-methylphenyl)methylidene]hydroxylamine Chemical compound CC1=CC(F)=CC=C1NC(C=C1Cl)=CC=C1C(=NO)C1=CC=CC=C1C VSCOXSDWLIBETA-UHFFFAOYSA-N 0.000 description 1
- XDOBUZFPBSEOEN-UHFFFAOYSA-N n-[[2-chloro-4-(4-fluoro-2-methylanilino)phenyl]-(3-fluoro-2-methylphenyl)methylidene]hydroxylamine Chemical compound CC1=CC(F)=CC=C1NC(C=C1Cl)=CC=C1C(=NO)C1=CC=CC(F)=C1C XDOBUZFPBSEOEN-UHFFFAOYSA-N 0.000 description 1
- LQTMMDRWVYQPQZ-UHFFFAOYSA-N n-[[2-chloro-4-(4-fluoro-n,2-dimethylanilino)phenyl]-(2-methylphenyl)methylidene]hydroxylamine Chemical compound C=1C=C(F)C=C(C)C=1N(C)C(C=C1Cl)=CC=C1C(=NO)C1=CC=CC=C1C LQTMMDRWVYQPQZ-UHFFFAOYSA-N 0.000 description 1
- WDXLZXXFSXIWHM-UHFFFAOYSA-N n-[[2-chloro-4-(4-phenylanilino)phenyl]-(2-methylphenyl)methylidene]hydroxylamine Chemical compound CC1=CC=CC=C1C(=NO)C(C(=C1)Cl)=CC=C1NC1=CC=C(C=2C=CC=CC=2)C=C1 WDXLZXXFSXIWHM-UHFFFAOYSA-N 0.000 description 1
- WJKOLXLGGSWFTB-UHFFFAOYSA-N n-[[2-chloro-4-(5-fluoro-2-methylanilino)phenyl]-(2-methylphenyl)methylidene]hydroxylamine Chemical compound CC1=CC=C(F)C=C1NC(C=C1Cl)=CC=C1C(=NO)C1=CC=CC=C1C WJKOLXLGGSWFTB-UHFFFAOYSA-N 0.000 description 1
- UJDMYOVFBJAJJR-UHFFFAOYSA-N n-[[2-chloro-4-[2-(trifluoromethyl)anilino]phenyl]-(2-methylphenyl)methylidene]hydroxylamine Chemical compound CC1=CC=CC=C1C(=NO)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1C(F)(F)F UJDMYOVFBJAJJR-UHFFFAOYSA-N 0.000 description 1
- YSOWLJSDHZSGLE-UHFFFAOYSA-N n-[[2-chloro-4-[3-(trifluoromethyl)anilino]phenyl]-(2-methylphenyl)methylidene]hydroxylamine Chemical compound CC1=CC=CC=C1C(=NO)C(C(=C1)Cl)=CC=C1NC1=CC=CC(C(F)(F)F)=C1 YSOWLJSDHZSGLE-UHFFFAOYSA-N 0.000 description 1
- HYYUTHLZXHOFDW-UHFFFAOYSA-N n-[[4-(2-bromoanilino)-2-chlorophenyl]-(2-methylphenyl)methylidene]hydroxylamine Chemical compound CC1=CC=CC=C1C(=NO)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1Br HYYUTHLZXHOFDW-UHFFFAOYSA-N 0.000 description 1
- JFCHDONGEQHLRO-UHFFFAOYSA-N n-[[4-(3-bromoanilino)-2-chlorophenyl]-(2-methylphenyl)methylidene]hydroxylamine Chemical compound CC1=CC=CC=C1C(=NO)C(C(=C1)Cl)=CC=C1NC1=CC=CC(Br)=C1 JFCHDONGEQHLRO-UHFFFAOYSA-N 0.000 description 1
- WHGHMLVQQCXRFV-UHFFFAOYSA-N n-[[4-(4-bromo-2,5-difluoroanilino)-2-chlorophenyl]-(2-methylphenyl)methylidene]hydroxylamine Chemical compound CC1=CC=CC=C1C(=NO)C(C(=C1)Cl)=CC=C1NC1=CC(F)=C(Br)C=C1F WHGHMLVQQCXRFV-UHFFFAOYSA-N 0.000 description 1
- HTIAGGAKZJPTCA-UHFFFAOYSA-N n-[[4-(4-bromo-2-chloroanilino)-2-chlorophenyl]-(2-methylphenyl)methylidene]hydroxylamine Chemical compound CC1=CC=CC=C1C(=NO)C(C(=C1)Cl)=CC=C1NC1=CC=C(Br)C=C1Cl HTIAGGAKZJPTCA-UHFFFAOYSA-N 0.000 description 1
- YLMQJLFGBVQKHA-UHFFFAOYSA-N n-[[4-(4-bromo-2-methylanilino)-2-chlorophenyl]-(2,5-dimethylphenyl)methylidene]hydroxylamine Chemical compound CC1=CC=C(C)C(C(=NO)C=2C(=CC(NC=3C(=CC(Br)=CC=3)C)=CC=2)Cl)=C1 YLMQJLFGBVQKHA-UHFFFAOYSA-N 0.000 description 1
- XJNNQYSRIYFRQA-UHFFFAOYSA-N n-[[4-(4-bromo-2-methylanilino)-2-chlorophenyl]-(2-methylphenyl)methylidene]hydroxylamine Chemical compound CC1=CC(Br)=CC=C1NC(C=C1Cl)=CC=C1C(=NO)C1=CC=CC=C1C XJNNQYSRIYFRQA-UHFFFAOYSA-N 0.000 description 1
- RKOWTGRYOQWDOB-UHFFFAOYSA-N n-[[4-(4-bromo-2-methylanilino)-2-chlorophenyl]-(3-chloro-2-methylphenyl)methylidene]hydroxylamine Chemical compound CC1=CC(Br)=CC=C1NC(C=C1Cl)=CC=C1C(=NO)C1=CC=CC(Cl)=C1C RKOWTGRYOQWDOB-UHFFFAOYSA-N 0.000 description 1
- LHBFJEIYGAHLFF-UHFFFAOYSA-N n-[[4-(4-bromo-2-methylanilino)-2-chlorophenyl]-(4-chloro-2-methylphenyl)methylidene]hydroxylamine Chemical compound CC1=CC(Br)=CC=C1NC(C=C1Cl)=CC=C1C(=NO)C1=CC=C(Cl)C=C1C LHBFJEIYGAHLFF-UHFFFAOYSA-N 0.000 description 1
- QNQIFCGVFCTSNE-UHFFFAOYSA-N n-[[4-(4-bromo-2-methylanilino)-2-chlorophenyl]-(4-ethoxy-2-methylphenyl)methylidene]hydroxylamine Chemical compound CC1=CC(OCC)=CC=C1C(=NO)C(C(=C1)Cl)=CC=C1NC1=CC=C(Br)C=C1C QNQIFCGVFCTSNE-UHFFFAOYSA-N 0.000 description 1
- UCLWTKYAIBXLGX-UHFFFAOYSA-N n-[[4-(4-bromo-2-methylanilino)-2-chlorophenyl]-(4-methoxy-2-methylphenyl)methylidene]hydroxylamine Chemical compound CC1=CC(OC)=CC=C1C(=NO)C(C(=C1)Cl)=CC=C1NC1=CC=C(Br)C=C1C UCLWTKYAIBXLGX-UHFFFAOYSA-N 0.000 description 1
- KKYFGIFIOZVIJH-UHFFFAOYSA-N n-[[4-(4-bromo-2-methylanilino)-2-fluorophenyl]-(2-methylphenyl)methylidene]hydroxylamine Chemical compound CC1=CC(Br)=CC=C1NC(C=C1F)=CC=C1C(=NO)C1=CC=CC=C1C KKYFGIFIOZVIJH-UHFFFAOYSA-N 0.000 description 1
- GPGKHUCYWKXTNY-UHFFFAOYSA-N n-[[4-(4-bromo-3-fluoroanilino)-2-chlorophenyl]-(2-methylphenyl)methylidene]hydroxylamine Chemical compound CC1=CC=CC=C1C(=NO)C(C(=C1)Cl)=CC=C1NC1=CC=C(Br)C(F)=C1 GPGKHUCYWKXTNY-UHFFFAOYSA-N 0.000 description 1
- BSALCRWXXFCQRT-UHFFFAOYSA-N n-[[4-(4-bromo-n-ethyl-2-methylanilino)-2-chlorophenyl]-(2-methylphenyl)methylidene]hydroxylamine Chemical compound C=1C=C(Br)C=C(C)C=1N(CC)C(C=C1Cl)=CC=C1C(=NO)C1=CC=CC=C1C BSALCRWXXFCQRT-UHFFFAOYSA-N 0.000 description 1
- MDKSSOFBQSXEBX-UHFFFAOYSA-N n-[[4-(4-bromoanilino)-2-chlorophenyl]-(2-methylphenyl)methylidene]hydroxylamine Chemical compound CC1=CC=CC=C1C(=NO)C(C(=C1)Cl)=CC=C1NC1=CC=C(Br)C=C1 MDKSSOFBQSXEBX-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 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 description 1
- 150000003873 salicylate salts Chemical class 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
- GECHUMIMRBOMGK-UHFFFAOYSA-N sulfapyridine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=CC=CC=N1 GECHUMIMRBOMGK-UHFFFAOYSA-N 0.000 description 1
- 229960002211 sulfapyridine Drugs 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- XDDVRYDDMGRFAZ-UHFFFAOYSA-N thiobenzophenone Chemical compound C=1C=CC=CC=1C(=S)C1=CC=CC=C1 XDDVRYDDMGRFAZ-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 235000019166 vitamin D Nutrition 0.000 description 1
- 239000011710 vitamin D Substances 0.000 description 1
- 150000003710 vitamin D derivatives Chemical class 0.000 description 1
- 229940046008 vitamin d Drugs 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US16933399P | 1999-12-06 | 1999-12-06 | |
| US60/169,333 | 1999-12-06 | ||
| PCT/DK2000/000653 WO2001042189A1 (en) | 1999-12-06 | 2000-11-29 | AMINOBENZOPHENONES AS INHIBITORS OF IL-1β AND TNF-$g(a) |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2003516377A JP2003516377A (ja) | 2003-05-13 |
| JP2003516377A5 true JP2003516377A5 (https=) | 2008-01-10 |
| JP4684515B2 JP4684515B2 (ja) | 2011-05-18 |
Family
ID=22615235
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2001543491A Expired - Fee Related JP4684515B2 (ja) | 1999-12-06 | 2000-11-29 | ＩＬ−１βおよびＴＮＦ−αの抑制剤としてのアミノベンゾフェノン |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US6541670B2 (https=) |
| EP (1) | EP1237845B1 (https=) |
| JP (1) | JP4684515B2 (https=) |
| KR (1) | KR20020071876A (https=) |
| CN (1) | CN1193003C (https=) |
| AT (1) | ATE362912T1 (https=) |
| AU (1) | AU776395B2 (https=) |
| BR (1) | BR0016164A (https=) |
| CA (1) | CA2393312C (https=) |
| CZ (1) | CZ20021940A3 (https=) |
| DE (1) | DE60034961T2 (https=) |
| ES (1) | ES2287040T3 (https=) |
| HU (1) | HUP0203813A3 (https=) |
| MX (1) | MXPA02005604A (https=) |
| NZ (1) | NZ519172A (https=) |
| PL (1) | PL356049A1 (https=) |
| RU (1) | RU2260422C2 (https=) |
| WO (1) | WO2001042189A1 (https=) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5763429A (en) * | 1993-09-10 | 1998-06-09 | Bone Care International, Inc. | Method of treating prostatic diseases using active vitamin D analogues |
| US6242434B1 (en) * | 1997-08-08 | 2001-06-05 | Bone Care International, Inc. | 24-hydroxyvitamin D, analogs and uses thereof |
| US20020128240A1 (en) * | 1996-12-30 | 2002-09-12 | Bone Care International, Inc. | Treatment of hyperproliferative diseases using active vitamin D analogues |
| US6566353B2 (en) * | 1996-12-30 | 2003-05-20 | Bone Care International, Inc. | Method of treating malignancy associated hypercalcemia using active vitamin D analogues |
| US6087350A (en) * | 1997-08-29 | 2000-07-11 | University Of Pittsburgh Of The Commonwealth System Of Higher Education | Use of pretreatment chemicals to enhance efficacy of cytotoxic agents |
| WO1999049870A1 (en) * | 1998-03-27 | 1999-10-07 | Oregon Health Sciences University | Vitamin d and its analogs in the treatment of tumors and other hyperproliferative disorders |
| AU2001260081B2 (en) | 2000-05-22 | 2005-07-28 | Leo Pharma A/S | Benzophenones as inhibitors of il-1beta and tnf-alpha |
| EP1301479A2 (en) * | 2000-07-18 | 2003-04-16 | Bone Care International, Inc. | STABILIZED 1$g(a)-HYDROXY VITAMIN D |
| WO2002018324A2 (en) | 2000-08-29 | 2002-03-07 | Nobex Corporation | Immunoregulatory compounds, derivatives thereof and their use |
| US20020165286A1 (en) * | 2000-12-08 | 2002-11-07 | Hanne Hedeman | Dermal anti-inflammatory composition |
| GB0107368D0 (en) * | 2001-03-23 | 2001-05-16 | Novartis Ag | Organic compounds |
| KR100896667B1 (ko) * | 2001-08-28 | 2009-05-14 | 레오 파마 에이/에스 | 신규한 아미노벤조페논 및 이를 포함하는 약제학적 조성물 |
| US8048924B2 (en) * | 2001-08-29 | 2011-11-01 | Biocon Limited | Methods and compositions employing 4-aminophenylacetic acid compounds |
| DE60310730T2 (de) | 2002-07-09 | 2007-05-16 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Pharmazeutische zusammensetzungen aus anticholinergica und p38 kinase hemmern zur behandlung von erkrankungen der atemwege |
| PL377377A1 (pl) * | 2002-12-20 | 2006-02-06 | Leo Pharma A/S | Nowe związki aminobenzofenonu |
| DK1658263T3 (da) * | 2003-07-24 | 2010-09-27 | Leo Pharma As | Aminobenzophenonforbindelser |
| US20060003950A1 (en) * | 2004-06-30 | 2006-01-05 | Bone Care International, Inc. | Method of treating prostatic diseases using a combination of vitamin D analogues and other agents |
| US7094775B2 (en) * | 2004-06-30 | 2006-08-22 | Bone Care International, Llc | Method of treating breast cancer using a combination of vitamin D analogues and other agents |
| DK1773767T3 (en) | 2004-07-07 | 2016-03-21 | Biocon Ltd | Synthesis of azo bound in immune regulatory relations |
| US20060035893A1 (en) | 2004-08-07 | 2006-02-16 | Boehringer Ingelheim International Gmbh | Pharmaceutical compositions for treatment of respiratory and gastrointestinal disorders |
| KR101260236B1 (ko) * | 2004-12-13 | 2013-05-06 | 레오 파마 에이/에스 | 트리아졸 치환된 아미노벤조페논 화합물 |
| PE20060777A1 (es) | 2004-12-24 | 2006-10-06 | Boehringer Ingelheim Int | Derivados de indolinona para el tratamiento o la prevencion de enfermedades fibroticas |
| EP1992344A1 (en) | 2007-05-18 | 2008-11-19 | Institut Curie | P38 alpha as a therapeutic target in pathologies linked to FGFR3 mutation |
| EP2206534A1 (de) | 2008-10-09 | 2010-07-14 | c-a-i-r biosciences GmbH | Dibenzocycloheptanonderivate und pharmazeutische Mittel, welche diese Verbindungen enthalten |
| NZ621655A (en) * | 2009-10-26 | 2015-08-28 | Nestec Sa | Assays for the detection of anti-tnf drugs and autoantibodies |
| EP2799537B1 (en) | 2011-12-28 | 2021-09-22 | Kyoto Prefectural Public University Corporation | Normalization of culture of corneal endothelial cells |
| WO2015050984A1 (en) | 2013-10-01 | 2015-04-09 | New York University | Amino, amido, and heterocyclic compounds as modulators of rage activity and uses thereof |
| WO2015072580A1 (ja) | 2013-11-14 | 2015-05-21 | 学校法人同志社 | 細胞増殖促進または細胞障害抑制による角膜内皮治療薬 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57177058A (en) | 1981-04-24 | 1982-10-30 | Hodogaya Chem Co Ltd | Novel fluoran compound |
| KR920702606A (ko) * | 1989-06-13 | 1992-10-06 | 스튜어트 알. 슈터 | 모노킨(Monokine)의 활성저해 |
| RU2037481C1 (ru) * | 1989-10-27 | 1995-06-19 | Американ Хоум Продактс Корпорейшн | Производные замещенной бензоилбензолбифенил- или 2-оксазолалкановой кислоты или их фармакологически приемлемые соли и способ их получения |
| JPH08104817A (ja) * | 1994-10-03 | 1996-04-23 | Nippon Soda Co Ltd | 新規なフルオラン化合物及びそれを用いた発色性記録材料 |
| GB9701453D0 (en) * | 1997-01-24 | 1997-03-12 | Leo Pharm Prod Ltd | Aminobenzophenones |
| US6455528B1 (en) * | 1997-10-14 | 2002-09-24 | Mitsubishi Pharma Corporation | Piperazine compounds and medicinal use thereof |
| JPH11217387A (ja) * | 1998-01-27 | 1999-08-10 | Yamada Chem Co Ltd | フルオラン化合物及びこれを用いた発色性記録材料 |
| AU768473B2 (en) * | 1999-07-16 | 2003-12-11 | Leo Pharmaceutical Products Ltd. A/S (Lovens Kemiske Fabrik Produktionsaktieselskab) | Novel aminobenzophenones |
| AU2001260081B2 (en) * | 2000-05-22 | 2005-07-28 | Leo Pharma A/S | Benzophenones as inhibitors of il-1beta and tnf-alpha |
-
2000
- 2000-11-29 MX MXPA02005604A patent/MXPA02005604A/es active IP Right Grant
- 2000-11-29 EP EP00979457A patent/EP1237845B1/en not_active Expired - Lifetime
- 2000-11-29 CA CA2393312A patent/CA2393312C/en not_active Expired - Fee Related
- 2000-11-29 CN CNB008177767A patent/CN1193003C/zh not_active Expired - Fee Related
- 2000-11-29 KR KR1020027007188A patent/KR20020071876A/ko not_active Ceased
- 2000-11-29 DE DE60034961T patent/DE60034961T2/de not_active Expired - Lifetime
- 2000-11-29 AU AU16935/01A patent/AU776395B2/en not_active Ceased
- 2000-11-29 PL PL00356049A patent/PL356049A1/xx not_active Application Discontinuation
- 2000-11-29 WO PCT/DK2000/000653 patent/WO2001042189A1/en not_active Ceased
- 2000-11-29 AT AT00979457T patent/ATE362912T1/de not_active IP Right Cessation
- 2000-11-29 BR BR0016164-0A patent/BR0016164A/pt not_active IP Right Cessation
- 2000-11-29 RU RU2002118113/15A patent/RU2260422C2/ru not_active IP Right Cessation
- 2000-11-29 CZ CZ20021940A patent/CZ20021940A3/cs unknown
- 2000-11-29 ES ES00979457T patent/ES2287040T3/es not_active Expired - Lifetime
- 2000-11-29 US US09/787,532 patent/US6541670B2/en not_active Expired - Lifetime
- 2000-11-29 HU HU0203813A patent/HUP0203813A3/hu unknown
- 2000-11-29 NZ NZ519172A patent/NZ519172A/en not_active IP Right Cessation
- 2000-11-29 JP JP2001543491A patent/JP4684515B2/ja not_active Expired - Fee Related
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2003516377A5 (https=) | ||
| CA2393312A1 (en) | Aminobenzophenones as inhibitors of il-1.beta. and tnf-.alpha. | |
| JP2002532415A5 (ja) | Ｍｅｋ阻害剤を含有する関節炎の治療用医薬組成物 | |
| CA2513092A1 (en) | Compounds for the treatment of metabolic disorders | |
| CZ2002158A3 (cs) | Aminobenzofenony jako inhibitory IL-1beta a TNF-alfa | |
| ZA200106650B (en) | Nitroxyderivatives having antiinflammatory, analgesic and antithrombotic activity. | |
| EP2593424A1 (en) | Novel arylamide derivatives having antiandrogenic properties | |
| RU2002103876A (ru) | АМИНОБЕНЗОФЕНОНЫ В КАЧЕСТВЕ ИНГИБИТОРОВ ИНТЕРЛЕЙКИНА IL-1β И ФАКТОРА НЕКРОЗА ОПУХОЛЕЙ TNF-α | |
| HUP0201911A2 (en) | Aminobenzophenones as inhibitors of il-1betha and tnf-alpha and pharmaceutical compositions containing them | |
| RU2331635C2 (ru) | Производные гидрокси-тетрагидро-нафталенилмочевины | |
| JP2003526663A (ja) | Ｃｏｍｔ阻害剤の鎮痛剤としての用途 | |
| RU2002103865A (ru) | Аминобензофеноны как ингибиторы ил-1β и TNF-α | |
| CA2379316A1 (en) | Novel aminobenzophenones | |
| HUP0201913A2 (en) | Aminobenzophenones as inhibitors of il-1 betha and tnf-alpha and pharmaceutical compositions containing them | |
| CZ288518B6 (cs) | Aminy, jejich použití a léčiva s jejich obsahem | |
| RU2015135369A (ru) | Биарил- или гетероциклические биарилзамещенные производные циклогексена в качестве ингибиторов сетр | |
| RU2001126547A (ru) | Производные дифенила | |
| US11807604B1 (en) | Pharmaceutical compounds, pharmaceutical compositions, and methods of treating asthma and other disorders | |
| US20070129433A1 (en) | Diphenylamine derivatives | |
| JP2012501353A (ja) | 抗炎症化合物 | |
| RU2006103364A (ru) | 2,4-бис (трифторэтокси) пиридиновое соединение и содержащее его лекарственное средство | |
| TWI334349B (en) | Pain threshold reduction depressant | |
| JP2002500187A (ja) | 多発性硬化症の治療方法 | |
| JPWO2006104172A1 (ja) | 関節リウマチの予防及び／又は治療薬 | |
| TWI303991B (en) | Use of nk-1 receptor antagonists for the treatment of brain,spinal or nerve injury |