JP4250204B2 - インターロイキンおよびｔｎｆの阻害剤としてのアミノベンゾフェノン類 - Google Patents

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Publication number

JP4250204B2

JP4250204B2 JP53149998A JP53149998A JP4250204B2 JP 4250204 B2 JP4250204 B2 JP 4250204B2 JP 53149998 A JP53149998 A JP 53149998A JP 53149998 A JP53149998 A JP 53149998A JP 4250204 B2 JP4250204 B2 JP 4250204B2

Authority

JP

Japan

Prior art keywords

compound

starting material

aminophenylamino

phenyl

general process

Prior art date

1997-01-24

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Expired - Fee Related

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• MAOBFOXLCJIFLV-UHFFFAOYSA-N (2-aminophenyl)-phenylmethanone Chemical class NC1=CC=CC=C1C(=O)C1=CC=CC=C1 MAOBFOXLCJIFLV-UHFFFAOYSA-N 0.000 title description 3
• 102000015696 Interleukins Human genes 0.000 title 1
• 108010063738 Interleukins Proteins 0.000 title 1
• 239000003112 inhibitor Substances 0.000 title 1
• 229940047122 interleukins Drugs 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 215
• -1 hydroxy, mercapto Chemical group 0.000 claims abstract description 26
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 20
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 15
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 15
• 239000001257 hydrogen Substances 0.000 claims abstract description 15
• 238000011282 treatment Methods 0.000 claims abstract description 15
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 15
• 125000003545 alkoxy group Chemical group 0.000 claims abstract description 11
• 125000003282 alkyl amino group Chemical group 0.000 claims abstract description 10
• 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 10
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 10
• 229910052736 halogen Inorganic materials 0.000 claims abstract description 10
• 150000002367 halogens Chemical group 0.000 claims abstract description 10
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 10
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 8
• 206010012438 Dermatitis atopic Diseases 0.000 claims abstract description 5
• 201000004681 Psoriasis Diseases 0.000 claims abstract description 5
• 208000006673 asthma Diseases 0.000 claims abstract description 5
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 5
• 201000008937 atopic dermatitis Diseases 0.000 claims abstract description 5
• 230000001684 chronic effect Effects 0.000 claims abstract description 5
• 239000003814 drug Substances 0.000 claims abstract description 5
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 5
• 229910052760 oxygen Inorganic materials 0.000 claims abstract description 5
• 239000001301 oxygen Substances 0.000 claims abstract description 5
• 206010039073 rheumatoid arthritis Diseases 0.000 claims abstract description 5
• 125000001424 substituent group Chemical group 0.000 claims abstract description 5
• 201000001320 Atherosclerosis Diseases 0.000 claims abstract description 4
• 201000005569 Gout Diseases 0.000 claims abstract description 4
• 206010020751 Hypersensitivity Diseases 0.000 claims abstract description 4
• 230000007815 allergy Effects 0.000 claims abstract description 4
• 230000002062 proliferating effect Effects 0.000 claims abstract description 4
• 201000005671 spondyloarthropathy Diseases 0.000 claims abstract description 4
• 208000026935 allergic disease Diseases 0.000 claims abstract description 3
• 208000022559 Inflammatory bowel disease Diseases 0.000 claims abstract 3
• 238000004519 manufacturing process Methods 0.000 claims description 70
• 239000004480 active ingredient Substances 0.000 claims description 18
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 15
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 13
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 12
• 238000000034 method Methods 0.000 claims description 10
• 150000003839 salts Chemical class 0.000 claims description 8
• MSXZXFPYTVQJIL-UHFFFAOYSA-N [4-(2-aminoanilino)-2-chlorophenyl]-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1N MSXZXFPYTVQJIL-UHFFFAOYSA-N 0.000 claims description 6
• 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
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
• 231100000252 nontoxic Toxicity 0.000 claims description 5
• 230000003000 nontoxic effect Effects 0.000 claims description 5
• 201000004624 Dermatitis Diseases 0.000 claims description 4
• 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
• XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 4
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 4
• 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 4
• LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims description 4
• 239000002904 solvent Substances 0.000 claims description 4
• JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 4
• CNCCIXVSTNKJNB-UHFFFAOYSA-N 1-[2-(4-benzoylanilino)phenyl]-3-propylurea Chemical compound CCCNC(=O)NC1=CC=CC=C1NC1=CC=C(C(=O)C=2C=CC=CC=2)C=C1 CNCCIXVSTNKJNB-UHFFFAOYSA-N 0.000 claims description 3
• UHTPDUNRQLNYOF-UHFFFAOYSA-N 3-[2-[3-chloro-4-(2-methylbenzoyl)anilino]phenyl]-1,1-dimethylurea Chemical compound CN(C)C(=O)NC1=CC=CC=C1NC(C=C1Cl)=CC=C1C(=O)C1=CC=CC=C1C UHTPDUNRQLNYOF-UHFFFAOYSA-N 0.000 claims description 3
• BWNBZGHUSFIPPF-UHFFFAOYSA-N [4-(2-aminoanilino)-2-chlorophenyl]-(2,6-dimethylphenyl)methanone Chemical compound CC1=CC=CC(C)=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1N BWNBZGHUSFIPPF-UHFFFAOYSA-N 0.000 claims description 3
• RZMXKJYAVMSCOU-UHFFFAOYSA-N [4-(2-aminoanilino)-2-methoxyphenyl]-(2-methylphenyl)methanone Chemical compound C=1C=C(C(=O)C=2C(=CC=CC=2)C)C(OC)=CC=1NC1=CC=CC=C1N RZMXKJYAVMSCOU-UHFFFAOYSA-N 0.000 claims description 3
• 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 claims description 3
• PKXPHBHIGIXLGC-UHFFFAOYSA-N [4-(2-aminoanilino)phenyl]-(4-phenylmethoxyphenyl)methanone Chemical compound NC1=CC=CC=C1NC1=CC=C(C(=O)C=2C=CC(OCC=3C=CC=CC=3)=CC=2)C=C1 PKXPHBHIGIXLGC-UHFFFAOYSA-N 0.000 claims description 3
• YBRFCGFHBWJQHP-UHFFFAOYSA-N [4-(2-aminoanilino)phenyl]-[2-(phenoxymethyl)phenyl]methanone Chemical compound NC1=CC=CC=C1NC1=CC=C(C(=O)C=2C(=CC=CC=2)COC=2C=CC=CC=2)C=C1 YBRFCGFHBWJQHP-UHFFFAOYSA-N 0.000 claims description 3
• 230000008878 coupling Effects 0.000 claims description 3
• 238000010168 coupling process Methods 0.000 claims description 3
• 238000005859 coupling reaction Methods 0.000 claims description 3
• MBGPOESHRVIAJA-UHFFFAOYSA-N n-[2-(4-benzoyl-n-(2,2,2-trifluoroacetyl)anilino)phenyl]-2,2,2-trifluoroacetamide Chemical compound FC(F)(F)C(=O)NC1=CC=CC=C1N(C(=O)C(F)(F)F)C1=CC=C(C(=O)C=2C=CC=CC=2)C=C1 MBGPOESHRVIAJA-UHFFFAOYSA-N 0.000 claims description 3
• 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 claims description 3
• FULXFPQLEOVYOF-UHFFFAOYSA-N n-[2-(4-benzoylanilino)phenyl]benzenesulfonamide Chemical compound C=1C=C(NC=2C(=CC=CC=2)NS(=O)(=O)C=2C=CC=CC=2)C=CC=1C(=O)C1=CC=CC=C1 FULXFPQLEOVYOF-UHFFFAOYSA-N 0.000 claims description 3
• BGGSPEBQBGRQQF-UHFFFAOYSA-N n-[2-(4-benzoylanilino)phenyl]ethanesulfonamide Chemical compound CCS(=O)(=O)NC1=CC=CC=C1NC1=CC=C(C(=O)C=2C=CC=CC=2)C=C1 BGGSPEBQBGRQQF-UHFFFAOYSA-N 0.000 claims description 3
• 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 claims description 3
• IUCHYNQLCQUEBG-UHFFFAOYSA-N n-[2-(4-benzoylanilino)phenyl]methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC=CC=C1NC1=CC=C(C(=O)C=2C=CC=CC=2)C=C1 IUCHYNQLCQUEBG-UHFFFAOYSA-N 0.000 claims description 3
• KIWXQPKZHFFGQG-UHFFFAOYSA-N n-[4-(4-benzoylanilino)phenyl]methanesulfonamide Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1NC1=CC=C(C(=O)C=2C=CC=CC=2)C=C1 KIWXQPKZHFFGQG-UHFFFAOYSA-N 0.000 claims description 3
• 239000008194 pharmaceutical composition Substances 0.000 claims description 3
• 239000000825 pharmaceutical preparation Substances 0.000 claims description 3
• 230000001225 therapeutic effect Effects 0.000 claims description 3
• LAVHQYRXHKYWTM-UHFFFAOYSA-N 1-[2-(4-benzoylanilino)phenyl]-3-phenylurea Chemical compound C=1C=CC=C(NC=2C=CC(=CC=2)C(=O)C=2C=CC=CC=2)C=1NC(=O)NC1=CC=CC=C1 LAVHQYRXHKYWTM-UHFFFAOYSA-N 0.000 claims description 2
• BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims description 2
• OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 2
• FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 2
• 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
• SRBYHMOZHJUQQB-UHFFFAOYSA-N [4-(2-aminoanilino)-2-chlorophenyl]-(4-fluoro-2-methylphenyl)methanone Chemical compound CC1=CC(F)=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1N SRBYHMOZHJUQQB-UHFFFAOYSA-N 0.000 claims description 2
• VRSHRKWRSBPEAE-UHFFFAOYSA-N [4-(2-aminoanilino)-2-chlorophenyl]-[2-(trifluoromethyl)phenyl]methanone Chemical compound NC1=CC=CC=C1NC(C=C1Cl)=CC=C1C(=O)C1=CC=CC=C1C(F)(F)F VRSHRKWRSBPEAE-UHFFFAOYSA-N 0.000 claims description 2
• WXJXPMUVXLOTQU-UHFFFAOYSA-N [4-(2-aminoanilino)phenyl]-(2,3-dihydro-1,4-benzodioxin-6-yl)methanone Chemical compound NC1=CC=CC=C1NC1=CC=C(C(=O)C=2C=C3OCCOC3=CC=2)C=C1 WXJXPMUVXLOTQU-UHFFFAOYSA-N 0.000 claims description 2
• 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 2
• 235000015165 citric acid Nutrition 0.000 claims description 2
• 235000019253 formic acid Nutrition 0.000 claims description 2
• XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 2
• 229940071870 hydroiodic acid Drugs 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
• 235000019260 propionic acid Nutrition 0.000 claims description 2
• 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 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
• 150000002431 hydrogen Chemical class 0.000 claims 9
• 239000002253 acid Substances 0.000 claims 4
• 239000003638 chemical reducing agent Substances 0.000 claims 2
• DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 claims 2
• TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 claims 1
• 229910021626 Tin(II) chloride Inorganic materials 0.000 claims 1
• 150000007513 acids Chemical class 0.000 claims 1
• 239000012752 auxiliary agent Substances 0.000 claims 1
• 230000002265 prevention Effects 0.000 claims 1
• 239000001119 stannous chloride Substances 0.000 claims 1
• 235000011150 stannous chloride Nutrition 0.000 claims 1
• LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
• 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 6
• 125000004122 cyclic group Chemical group 0.000 abstract description 4
• 230000000699 topical effect Effects 0.000 abstract description 3
• 230000002757 inflammatory effect Effects 0.000 abstract description 2
• 208000017520 skin disease Diseases 0.000 abstract description 2
• 230000009885 systemic effect Effects 0.000 abstract description 2
• 238000011321 prophylaxis Methods 0.000 abstract 1
• 229940124597 therapeutic agent Drugs 0.000 abstract 1
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 249
• 239000007858 starting material Substances 0.000 description 205
• 230000008570 general process Effects 0.000 description 148
• 238000000746 purification Methods 0.000 description 116
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 101
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 99
• OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 98
• 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 89
• 238000004587 chromatography analysis Methods 0.000 description 80
• 239000003480 eluent Substances 0.000 description 77
• IMNFDUFMRHMDMM-UHFFFAOYSA-N anhydrous n-heptane Natural products CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 72
• 238000005160 1H NMR spectroscopy Methods 0.000 description 68
• PWKNBLFSJAVFAB-UHFFFAOYSA-N 1-fluoro-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1F PWKNBLFSJAVFAB-UHFFFAOYSA-N 0.000 description 50
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 43
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
• 239000000203 mixture Substances 0.000 description 26
• 238000001665 trituration Methods 0.000 description 24
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
• 239000011541 reaction mixture Substances 0.000 description 21
• 239000000243 solution Substances 0.000 description 20
• 238000002425 crystallisation Methods 0.000 description 19
• 230000008025 crystallization Effects 0.000 description 19
• 238000009472 formulation Methods 0.000 description 17
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
• WFOVEDJTASPCIR-UHFFFAOYSA-N 3-[(4-methyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)methylamino]-n-[[2-(trifluoromethyl)phenyl]methyl]benzamide Chemical compound N=1N=C(C=2C=CN=CC=2)N(C)C=1CNC(C=1)=CC=CC=1C(=O)NCC1=CC=CC=C1C(F)(F)F WFOVEDJTASPCIR-UHFFFAOYSA-N 0.000 description 13
• RAWYMBACZSQNDD-UHFFFAOYSA-N [4-(2-aminoanilino)phenyl]-phenylmethanone Chemical compound NC1=CC=CC=C1NC1=CC=C(C(=O)C=2C=CC=CC=2)C=C1 RAWYMBACZSQNDD-UHFFFAOYSA-N 0.000 description 12
• FFBHFFJDDLITSX-UHFFFAOYSA-N benzyl N-[2-hydroxy-4-(3-oxomorpholin-4-yl)phenyl]carbamate Chemical compound OC1=C(NC(=O)OCC2=CC=CC=C2)C=CC(=C1)N1CCOCC1=O FFBHFFJDDLITSX-UHFFFAOYSA-N 0.000 description 12
• 239000012043 crude product Substances 0.000 description 12
• 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
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
• 230000015572 biosynthetic process Effects 0.000 description 9
• 239000002244 precipitate Substances 0.000 description 9
• 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 8
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
• 210000004027 cell Anatomy 0.000 description 7
• 239000012074 organic phase Substances 0.000 description 7
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
• 108060008682 Tumor Necrosis Factor Proteins 0.000 description 6
• 102000000852 Tumor Necrosis Factor-alpha Human genes 0.000 description 6
• 238000001914 filtration Methods 0.000 description 6
• INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 6
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