JP4540984B2 - 新規アミノベンゾフェノン - Google Patents
新規アミノベンゾフェノン Download PDFInfo
- Publication number
- JP4540984B2 JP4540984B2 JP2003523200A JP2003523200A JP4540984B2 JP 4540984 B2 JP4540984 B2 JP 4540984B2 JP 2003523200 A JP2003523200 A JP 2003523200A JP 2003523200 A JP2003523200 A JP 2003523200A JP 4540984 B2 JP4540984 B2 JP 4540984B2
- Authority
- JP
- Japan
- Prior art keywords
- phenyl
- amino
- chloro
- methylphenyl
- methanone
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- MAOBFOXLCJIFLV-UHFFFAOYSA-N (2-aminophenyl)-phenylmethanone Chemical compound NC1=CC=CC=C1C(=O)C1=CC=CC=C1 MAOBFOXLCJIFLV-UHFFFAOYSA-N 0.000 title abstract description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 413
- -1 2- (2-{[3-chloro-4- (2-methylbenzoyl) phenyl] amino} phenyl) ethyl Chemical group 0.000 claims description 137
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 29
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 21
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 18
- AVJDYXLMKWKGBA-UHFFFAOYSA-N [4-[4-bromo-2-(2-hydroxyethoxymethyl)anilino]-2-chlorophenyl]-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=C(Br)C=C1COCCO AVJDYXLMKWKGBA-UHFFFAOYSA-N 0.000 claims description 14
- AQEXUXIKCRBBTI-UHFFFAOYSA-N [2-chloro-4-[2-(2-hydroxyethyl)anilino]phenyl]-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1CCO AQEXUXIKCRBBTI-UHFFFAOYSA-N 0.000 claims description 13
- JFUAFGPNYRFZLM-RMKNXTFCSA-N [4-[2-[(e)-3-aminoprop-1-enyl]anilino]-2-chlorophenyl]-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1\C=C\CN JFUAFGPNYRFZLM-RMKNXTFCSA-N 0.000 claims description 11
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 10
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 9
- 229940022663 acetate Drugs 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- JFPGKEOODBKLDU-UHFFFAOYSA-N 1-[2-[3-chloro-4-(2-methylbenzoyl)anilino]phenyl]propan-2-yl acetate Chemical compound CC(=O)OC(C)CC1=CC=CC=C1NC(C=C1Cl)=CC=C1C(=O)C1=CC=CC=C1C JFPGKEOODBKLDU-UHFFFAOYSA-N 0.000 claims description 6
- COBTVLLYFAQVRY-UHFFFAOYSA-N [2-chloro-4-[2-(2-hydroxyethoxymethyl)anilino]phenyl]-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1COCCO COBTVLLYFAQVRY-UHFFFAOYSA-N 0.000 claims description 6
- QJNDYVOPQXQBNY-UHFFFAOYSA-N [2-chloro-4-[2-(3-hydroxypropoxy)anilino]phenyl]-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1OCCCO QJNDYVOPQXQBNY-UHFFFAOYSA-N 0.000 claims description 6
- OXQJRCMVWRSKIU-UHFFFAOYSA-N [2-chloro-4-[2-(diethoxyphosphorylmethyl)anilino]phenyl]-(2-methylphenyl)methanone Chemical compound CCOP(=O)(OCC)CC1=CC=CC=C1NC(C=C1Cl)=CC=C1C(=O)C1=CC=CC=C1C OXQJRCMVWRSKIU-UHFFFAOYSA-N 0.000 claims description 6
- XYINPYRVKHCBQB-UHFFFAOYSA-N [4-[2-(aminomethyl)anilino]-2-chlorophenyl]-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1CN XYINPYRVKHCBQB-UHFFFAOYSA-N 0.000 claims description 6
- XPYLTEPNMPTZHK-FMIVXFBMSA-N 1-[(e)-3-[2-[3-chloro-4-(2-methylbenzoyl)anilino]phenyl]prop-2-enyl]-3-cyclohexylurea Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1\C=C\CNC(=O)NC1CCCCC1 XPYLTEPNMPTZHK-FMIVXFBMSA-N 0.000 claims description 5
- RYSROKNDIDHZJI-FMIVXFBMSA-N 1-tert-butyl-3-[(e)-3-[2-[3-chloro-4-(2-methylbenzoyl)anilino]phenyl]prop-2-enyl]thiourea Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1\C=C\CNC(=S)NC(C)(C)C RYSROKNDIDHZJI-FMIVXFBMSA-N 0.000 claims description 5
- CJPJIIPRRZLRNR-JXMROGBWSA-N 2-[1-[(e)-3-[2-[3-chloro-4-(2-methylbenzoyl)anilino]phenyl]prop-2-enyl]piperidin-4-yl]ethyl acetate Chemical compound C1CC(CCOC(=O)C)CCN1C\C=C\C1=CC=CC=C1NC(C=C1Cl)=CC=C1C(=O)C1=CC=CC=C1C CJPJIIPRRZLRNR-JXMROGBWSA-N 0.000 claims description 5
- KFKXIYKEYLVBBL-DHZHZOJOSA-N 2-[2-acetyloxyethyl-[(e)-3-[2-[3-chloro-4-(2-methylbenzoyl)anilino]phenyl]prop-2-enyl]amino]ethyl acetate Chemical compound CC(=O)OCCN(CCOC(C)=O)C\C=C\C1=CC=CC=C1NC(C=C1Cl)=CC=C1C(=O)C1=CC=CC=C1C KFKXIYKEYLVBBL-DHZHZOJOSA-N 0.000 claims description 5
- KOSFPIUIERYHRN-UHFFFAOYSA-N 2-[[2-[3-chloro-4-(2-methylbenzoyl)anilino]phenyl]methyl]isoindole-1,3-dione Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1CN1C(=O)C2=CC=CC=C2C1=O KOSFPIUIERYHRN-UHFFFAOYSA-N 0.000 claims description 5
- CSZLAGIWFMBBMI-UHFFFAOYSA-N 2-[[5-bromo-2-[3-chloro-4-(2-methylbenzoyl)anilino]phenyl]methoxy]ethyl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OCCOCC1=CC(Br)=CC=C1NC(C=C1Cl)=CC=C1C(=O)C1=CC=CC=C1C CSZLAGIWFMBBMI-UHFFFAOYSA-N 0.000 claims description 5
- GXFWGLFVQPHTNC-UHFFFAOYSA-N 4-[2-[2-[3-chloro-4-(2-methylbenzoyl)anilino]phenyl]ethoxy]-4-oxobutanoic acid Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1CCOC(=O)CCC(O)=O GXFWGLFVQPHTNC-UHFFFAOYSA-N 0.000 claims description 5
- LWZGMWIWPHBAKE-UHFFFAOYSA-N [2-chloro-4-[2-(2-hydroxypropyl)anilino]phenyl]-(2-methylphenyl)methanone Chemical compound CC(O)CC1=CC=CC=C1NC(C=C1Cl)=CC=C1C(=O)C1=CC=CC=C1C LWZGMWIWPHBAKE-UHFFFAOYSA-N 0.000 claims description 5
- FKAKZFHOHZVOLC-UHFFFAOYSA-N [2-chloro-4-[2-(2-iodoethoxymethyl)anilino]phenyl]-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1COCCI FKAKZFHOHZVOLC-UHFFFAOYSA-N 0.000 claims description 5
- XFFBBCSESUJDNO-UHFFFAOYSA-N [2-chloro-4-[2-(3,3,3-trifluoropropoxymethyl)anilino]phenyl]-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1COCCC(F)(F)F XFFBBCSESUJDNO-UHFFFAOYSA-N 0.000 claims description 5
- UQOGBJHKQSJAOQ-UHFFFAOYSA-N [2-chloro-4-[2-(3-hydroxypropyl)anilino]phenyl]-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1CCCO UQOGBJHKQSJAOQ-UHFFFAOYSA-N 0.000 claims description 5
- NUCUIYGJDKXZST-CCEZHUSRSA-N [2-chloro-4-[2-[(e)-3-hydroxy-3-methylbut-1-enyl]anilino]phenyl]-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1\C=C\C(C)(C)O NUCUIYGJDKXZST-CCEZHUSRSA-N 0.000 claims description 5
- UDMUMCMGVXOTKJ-RMKNXTFCSA-N [2-chloro-4-[2-[(e)-3-hydroxyprop-1-enyl]anilino]phenyl]-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1\C=C\CO UDMUMCMGVXOTKJ-RMKNXTFCSA-N 0.000 claims description 5
- KTMQZZJSCFPLMM-RMKNXTFCSA-N [2-chloro-4-[2-[(e)-3-morpholin-4-ylprop-1-enyl]anilino]phenyl]-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1\C=C\CN1CCOCC1 KTMQZZJSCFPLMM-RMKNXTFCSA-N 0.000 claims description 5
- PDIPQSUMQLMPMJ-UHFFFAOYSA-N [2-chloro-4-[2-[2-(2-hydroxyethoxy)ethoxymethyl]anilino]phenyl]-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1COCCOCCO PDIPQSUMQLMPMJ-UHFFFAOYSA-N 0.000 claims description 5
- VVMJQNVGIRFNNN-UHFFFAOYSA-N [2-chloro-4-[2-[2-[2-(oxan-2-yloxy)ethoxy]ethoxymethyl]anilino]phenyl]-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1COCCOCCOC1OCCCC1 VVMJQNVGIRFNNN-UHFFFAOYSA-N 0.000 claims description 5
- PKCIXQGQZBYYTQ-UHFFFAOYSA-N [2-chloro-4-[2-[3-(oxan-2-yloxy)propoxy]anilino]phenyl]-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1OCCCOC1OCCCC1 PKCIXQGQZBYYTQ-UHFFFAOYSA-N 0.000 claims description 5
- UUWUJULUPQOGHD-UHFFFAOYSA-N [2-chloro-4-[2-[3-(oxan-2-yloxy)propoxymethyl]anilino]phenyl]-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1COCCCOC1OCCCC1 UUWUJULUPQOGHD-UHFFFAOYSA-N 0.000 claims description 5
- NULCISDQBUADCK-UHFFFAOYSA-N [4-[4-bromo-2-(2-iodoethoxymethyl)anilino]-2-chlorophenyl]-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=C(Br)C=C1COCCI NULCISDQBUADCK-UHFFFAOYSA-N 0.000 claims description 5
- XFTJYHJVCHZYBM-UHFFFAOYSA-N [4-[4-bromo-2-[2-(2-hydroxyethoxy)ethoxymethyl]anilino]-2-chlorophenyl]-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=C(Br)C=C1COCCOCCO XFTJYHJVCHZYBM-UHFFFAOYSA-N 0.000 claims description 5
- OSGAAUHVJDRMFG-UHFFFAOYSA-N [4-[4-bromo-2-[2-(2-iodoethoxy)ethoxymethyl]anilino]-2-chlorophenyl]-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=C(Br)C=C1COCCOCCI OSGAAUHVJDRMFG-UHFFFAOYSA-N 0.000 claims description 5
- PFTMLRHSNFPNOG-UHFFFAOYSA-N [4-[4-bromo-2-[2-[2-(2-hydroxyethoxy)ethoxy]ethoxymethyl]anilino]-2-chlorophenyl]-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=C(Br)C=C1COCCOCCOCCO PFTMLRHSNFPNOG-UHFFFAOYSA-N 0.000 claims description 5
- IXCLKUJQTNNPQM-UHFFFAOYSA-N [4-[4-bromo-2-[2-[2-(2-iodoethoxy)ethoxy]ethoxymethyl]anilino]-2-chlorophenyl]-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=C(Br)C=C1COCCOCCOCCI IXCLKUJQTNNPQM-UHFFFAOYSA-N 0.000 claims description 5
- ITXSLCZPKOJHKM-UHFFFAOYSA-N n'-[2-[3-chloro-4-(2-methylbenzoyl)anilino]phenyl]-n-(6-hydroxyhexyl)butanediamide Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1NC(=O)CCC(=O)NCCCCCCO ITXSLCZPKOJHKM-UHFFFAOYSA-N 0.000 claims description 5
- ZAKPKHQMZLLVTC-JXMROGBWSA-N n-[(e)-3-[2-[3-chloro-4-(2-methylbenzoyl)anilino]phenyl]prop-2-enyl]-4-oxopentanamide Chemical compound CC(=O)CCC(=O)NC\C=C\C1=CC=CC=C1NC(C=C1Cl)=CC=C1C(=O)C1=CC=CC=C1C ZAKPKHQMZLLVTC-JXMROGBWSA-N 0.000 claims description 5
- UEELGLGKUMDWQK-UHFFFAOYSA-N n-[[2-[3-chloro-4-(2-methylbenzoyl)anilino]phenyl]methyl]-2-diethoxyphosphorylacetamide Chemical compound CCOP(=O)(OCC)CC(=O)NCC1=CC=CC=C1NC(C=C1Cl)=CC=C1C(=O)C1=CC=CC=C1C UEELGLGKUMDWQK-UHFFFAOYSA-N 0.000 claims description 5
- RZWCUNNVHPRHEE-UHFFFAOYSA-N 1-[2-[2-[3-chloro-4-(2-methylbenzoyl)anilino]phenyl]ethyl]piperidine-2,6-dione Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1CCN1C(=O)CCCC1=O RZWCUNNVHPRHEE-UHFFFAOYSA-N 0.000 claims description 4
- BMJKBOXGLHNRMG-UHFFFAOYSA-N 1-[2-[3-chloro-4-(2-methylbenzoyl)anilino]phenyl]pyrrolidine-2,5-dione Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1N1C(=O)CCC1=O BMJKBOXGLHNRMG-UHFFFAOYSA-N 0.000 claims description 4
- YMROMRJRSLUTOM-UHFFFAOYSA-N 1-[2-[[5-bromo-2-[3-chloro-4-(2-methylbenzoyl)anilino]phenyl]methoxy]ethyl]pyrrolidine-2,5-dione Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=C(Br)C=C1COCCN1C(=O)CCC1=O YMROMRJRSLUTOM-UHFFFAOYSA-N 0.000 claims description 4
- WFQHSZANBLMBPZ-UHFFFAOYSA-N 1-[3-[2-[2-[3-chloro-4-(2-methylbenzoyl)anilino]phenyl]ethylamino]propyl]pyrrolidin-2-one Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1CCNCCCN1C(=O)CCC1 WFQHSZANBLMBPZ-UHFFFAOYSA-N 0.000 claims description 4
- PXHPHZOZEUGBMZ-UHFFFAOYSA-N 2-phenylethyl n-[2-[3-chloro-4-(2-methylbenzoyl)anilino]phenyl]carbamate Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1NC(=O)OCCC1=CC=CC=C1 PXHPHZOZEUGBMZ-UHFFFAOYSA-N 0.000 claims description 4
- NNZZVRROPKCPGG-UHFFFAOYSA-N 3-[2-[[5-bromo-2-[3-chloro-4-(2-methylbenzoyl)anilino]phenyl]methoxy]ethyl]imidazolidine-2,4-dione Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=C(Br)C=C1COCCN1C(=O)NCC1=O NNZZVRROPKCPGG-UHFFFAOYSA-N 0.000 claims description 4
- PPXMCTKVIGKWKP-UHFFFAOYSA-N 4-[2-[2-[3-chloro-4-(2-methylbenzoyl)anilino]phenyl]ethyl]morpholine-3,5-dione Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1CCN1C(=O)COCC1=O PPXMCTKVIGKWKP-UHFFFAOYSA-N 0.000 claims description 4
- XELONKVQFGEAJV-UHFFFAOYSA-N 4-[2-[[5-bromo-2-[3-chloro-4-(2-methylbenzoyl)anilino]phenyl]methoxy]ethyl]morpholine-3,5-dione Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=C(Br)C=C1COCCN1C(=O)COCC1=O XELONKVQFGEAJV-UHFFFAOYSA-N 0.000 claims description 4
- YOHHMUHECKKHSO-UHFFFAOYSA-N 6-[[4-[2-[3-chloro-4-(2-methylbenzoyl)anilino]anilino]-4-oxobutanoyl]amino]hexyl diethyl phosphate Chemical compound CCOP(=O)(OCC)OCCCCCCNC(=O)CCC(=O)NC1=CC=CC=C1NC(C=C1Cl)=CC=C1C(=O)C1=CC=CC=C1C YOHHMUHECKKHSO-UHFFFAOYSA-N 0.000 claims description 4
- ODLLIVVLGBEBBU-ISILISOKSA-N [(3s,4r)-4-acetyloxy-1-[2-[[5-bromo-2-[3-chloro-4-(2-methylbenzoyl)anilino]phenyl]methoxy]ethyl]-2,5-dioxopyrrolidin-3-yl] acetate Chemical compound O=C1[C@@H](OC(=O)C)[C@@H](OC(C)=O)C(=O)N1CCOCC1=CC(Br)=CC=C1NC(C=C1Cl)=CC=C1C(=O)C1=CC=CC=C1C ODLLIVVLGBEBBU-ISILISOKSA-N 0.000 claims description 4
- TVDGPILBCCYQDT-UHFFFAOYSA-N [2-[2-[3-chloro-4-(2-methylbenzoyl)anilino]anilino]-2-oxoethyl] acetate Chemical compound CC(=O)OCC(=O)NC1=CC=CC=C1NC(C=C1Cl)=CC=C1C(=O)C1=CC=CC=C1C TVDGPILBCCYQDT-UHFFFAOYSA-N 0.000 claims description 4
- ZFTRXOHRPWHONP-UHFFFAOYSA-N [2-[3-chloro-4-(2-methylbenzoyl)anilino]phenyl]methylphosphonic acid Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1CP(O)(O)=O ZFTRXOHRPWHONP-UHFFFAOYSA-N 0.000 claims description 4
- QGROFRDWLVHLJJ-UHFFFAOYSA-N [2-[[2-[3-chloro-4-(2-methylbenzoyl)anilino]phenyl]methylamino]-2-oxoethyl]phosphonic acid Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1CNC(=O)CP(O)(O)=O QGROFRDWLVHLJJ-UHFFFAOYSA-N 0.000 claims description 4
- NDKXFNRRNWLTOB-UHFFFAOYSA-N [2-chloro-4-[2-(2-morpholin-4-ylethyl)anilino]phenyl]-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1CCN1CCOCC1 NDKXFNRRNWLTOB-UHFFFAOYSA-N 0.000 claims description 4
- RRSFHQAHCUJBHL-UHFFFAOYSA-N [2-chloro-4-[2-(3-hydroxypropoxymethyl)anilino]phenyl]-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1COCCCO RRSFHQAHCUJBHL-UHFFFAOYSA-N 0.000 claims description 4
- WRXKBZQHBPVHRZ-UHFFFAOYSA-N [2-chloro-4-[2-(3-morpholin-4-ylpropoxy)anilino]phenyl]-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1OCCCN1CCOCC1 WRXKBZQHBPVHRZ-UHFFFAOYSA-N 0.000 claims description 4
- ZJTOJZDPLYKOAU-RMKNXTFCSA-N [2-chloro-4-[2-[(e)-3-[4-(2-hydroxyethyl)piperidin-1-yl]prop-1-enyl]anilino]phenyl]-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1\C=C\CN1CCC(CCO)CC1 ZJTOJZDPLYKOAU-RMKNXTFCSA-N 0.000 claims description 4
- JFZBWOMYLXOISH-RDIUEAQDSA-N [2-chloro-4-[2-[(e)-3-[[(2r,3s,4r,5r)-3,4-dihydroxy-5-methoxyoxolan-2-yl]methoxy]prop-1-enyl]anilino]phenyl]-(2-methylphenyl)methanone Chemical compound O[C@H]1[C@@H](O)[C@H](OC)O[C@@H]1COC\C=C\C1=CC=CC=C1NC(C=C1Cl)=CC=C1C(=O)C1=CC=CC=C1C JFZBWOMYLXOISH-RDIUEAQDSA-N 0.000 claims description 4
- SVRDBGWQNMQEOR-UXBLZVDNSA-N [2-chloro-4-[2-[(e)-4-hydroxybut-1-enyl]anilino]phenyl]-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1\C=C\CCO SVRDBGWQNMQEOR-UXBLZVDNSA-N 0.000 claims description 4
- KSPIAUMASCIUMD-UHFFFAOYSA-N [2-chloro-4-[2-[2-(2,3-dihydroxypropylamino)ethyl]anilino]phenyl]-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1CCNCC(O)CO KSPIAUMASCIUMD-UHFFFAOYSA-N 0.000 claims description 4
- NTLRZVOLQGREDX-UHFFFAOYSA-N [2-chloro-4-[2-[2-(2-methoxyethylamino)ethyl]anilino]phenyl]-(2-methylphenyl)methanone Chemical compound COCCNCCC1=CC=CC=C1NC(C=C1Cl)=CC=C1C(=O)C1=CC=CC=C1C NTLRZVOLQGREDX-UHFFFAOYSA-N 0.000 claims description 4
- DJNOKUPKSWCZCS-UHFFFAOYSA-N [2-chloro-4-[2-[2-(4-methylpiperazin-1-yl)ethyl]anilino]phenyl]-(2-methylphenyl)methanone Chemical compound C1CN(C)CCN1CCC1=CC=CC=C1NC(C=C1Cl)=CC=C1C(=O)C1=CC=CC=C1C DJNOKUPKSWCZCS-UHFFFAOYSA-N 0.000 claims description 4
- DKEPJJPFNUZKIO-UHFFFAOYSA-N [2-chloro-4-[2-[2-(oxolan-2-ylmethylamino)ethyl]anilino]phenyl]-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1CCNCC1OCCC1 DKEPJJPFNUZKIO-UHFFFAOYSA-N 0.000 claims description 4
- JBVVZYRHOIGKAQ-UHFFFAOYSA-N [2-chloro-4-[2-[2-[(2,2-dimethyl-1,3-dioxolan-4-yl)methylamino]ethyl]anilino]phenyl]-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1CCNCC1OC(C)(C)OC1 JBVVZYRHOIGKAQ-UHFFFAOYSA-N 0.000 claims description 4
- UKXMOHJCRFYPKZ-UHFFFAOYSA-N [2-chloro-4-[2-[2-[2-(dimethylamino)ethylamino]ethyl]anilino]phenyl]-(2-methylphenyl)methanone Chemical compound CN(C)CCNCCC1=CC=CC=C1NC(C=C1Cl)=CC=C1C(=O)C1=CC=CC=C1C UKXMOHJCRFYPKZ-UHFFFAOYSA-N 0.000 claims description 4
- UJFMINQOZPVJLO-UHFFFAOYSA-N [2-chloro-4-[2-[2-[4-(2-methoxyethyl)piperazin-1-yl]ethyl]anilino]phenyl]-(2-methylphenyl)methanone Chemical compound C1CN(CCOC)CCN1CCC1=CC=CC=C1NC(C=C1Cl)=CC=C1C(=O)C1=CC=CC=C1C UJFMINQOZPVJLO-UHFFFAOYSA-N 0.000 claims description 4
- WXVGFWDXCCYEPR-RMKNXTFCSA-N [4-[2-[(e)-3-[bis(2-hydroxyethyl)amino]prop-1-enyl]anilino]-2-chlorophenyl]-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1\C=C\CN(CCO)CCO WXVGFWDXCCYEPR-RMKNXTFCSA-N 0.000 claims description 4
- JCZZHMWVHXQXHU-UHFFFAOYSA-N [4-[4-bromo-2-(2-hydroxyethyl)anilino]-2-chlorophenyl]-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=C(Br)C=C1CCO JCZZHMWVHXQXHU-UHFFFAOYSA-N 0.000 claims description 4
- DXWSPIXAFVZGHT-UHFFFAOYSA-N [4-[4-bromo-2-(3,3,3-trifluoropropoxymethyl)anilino]-2-chlorophenyl]-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=C(Br)C=C1COCCC(F)(F)F DXWSPIXAFVZGHT-UHFFFAOYSA-N 0.000 claims description 4
- OGBVRMYSNSKIEF-UHFFFAOYSA-L benzyl-dioxido-oxo-$l^{5}-phosphane Chemical compound [O-]P([O-])(=O)CC1=CC=CC=C1 OGBVRMYSNSKIEF-UHFFFAOYSA-L 0.000 claims description 4
- SNCZNSNPXMPCGN-UHFFFAOYSA-N butanediamide Chemical compound NC(=O)CCC(N)=O SNCZNSNPXMPCGN-UHFFFAOYSA-N 0.000 claims description 4
- ATGDOXJDPFRJPI-UHFFFAOYSA-N n'-[2-[3-chloro-4-(2-methylbenzoyl)anilino]phenyl]-n-(2,3-dihydroxypropyl)butanediamide Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1NC(=O)CCC(=O)NCC(O)CO ATGDOXJDPFRJPI-UHFFFAOYSA-N 0.000 claims description 4
- ZOLPEBVPKJNOMH-UHFFFAOYSA-N n'-[2-[3-chloro-4-(2-methylbenzoyl)anilino]phenyl]-n-(4-phenoxybutyl)butanediamide Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1NC(=O)CCC(=O)NCCCCOC1=CC=CC=C1 ZOLPEBVPKJNOMH-UHFFFAOYSA-N 0.000 claims description 4
- XGXYMJHEYXZLMP-UHFFFAOYSA-N n'-[5-bromo-2-[3-chloro-4-(2-methylbenzoyl)anilino]phenyl]-n-(6-hydroxyhexyl)butanediamide Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=C(Br)C=C1NC(=O)CCC(=O)NCCCCCCO XGXYMJHEYXZLMP-UHFFFAOYSA-N 0.000 claims description 4
- PNBZPYJGHSNMLZ-UHFFFAOYSA-N n-[2-[3-chloro-4-(2-methylbenzoyl)anilino]phenyl]-2-(1,3-dioxoisoindol-2-yl)acetamide Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1NC(=O)CN1C(=O)C2=CC=CC=C2C1=O PNBZPYJGHSNMLZ-UHFFFAOYSA-N 0.000 claims description 4
- KQIVIHYEWZURJE-UHFFFAOYSA-N n-[2-[3-chloro-4-(2-methylbenzoyl)anilino]phenyl]-2-phenoxyacetamide Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1NC(=O)COC1=CC=CC=C1 KQIVIHYEWZURJE-UHFFFAOYSA-N 0.000 claims description 4
- VPWXAHSRVLNJSH-UHFFFAOYSA-N n-[2-[3-chloro-4-(2-methylbenzoyl)anilino]phenyl]-3-phenoxypropanamide Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1NC(=O)CCOC1=CC=CC=C1 VPWXAHSRVLNJSH-UHFFFAOYSA-N 0.000 claims description 4
- PJJFHEJUYZFWNP-UHFFFAOYSA-N n-[2-[3-chloro-4-(2-methylbenzoyl)anilino]phenyl]benzenesulfonamide Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1NS(=O)(=O)C1=CC=CC=C1 PJJFHEJUYZFWNP-UHFFFAOYSA-N 0.000 claims description 4
- DXWVFCUYNUGRRS-UHFFFAOYSA-N n-[5-bromo-2-[3-chloro-4-(2-methylbenzoyl)anilino]phenyl]-2,2,2-trifluoroethanesulfonamide Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=C(Br)C=C1NS(=O)(=O)CC(F)(F)F DXWVFCUYNUGRRS-UHFFFAOYSA-N 0.000 claims description 4
- LZEVFMLEWXZBFJ-UHFFFAOYSA-N n-[5-bromo-2-[3-chloro-4-(2-methylbenzoyl)anilino]phenyl]-2-diethoxyphosphorylacetamide Chemical compound CCOP(=O)(OCC)CC(=O)NC1=CC(Br)=CC=C1NC(C=C1Cl)=CC=C1C(=O)C1=CC=CC=C1C LZEVFMLEWXZBFJ-UHFFFAOYSA-N 0.000 claims description 4
- VBWGTFYHSBSYNK-UHFFFAOYSA-N n-[[2-[3-chloro-4-(2-methylbenzoyl)anilino]phenyl]methyl]-2,2,2-trifluoroethanesulfonamide Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1CNS(=O)(=O)CC(F)(F)F VBWGTFYHSBSYNK-UHFFFAOYSA-N 0.000 claims description 4
- 239000012453 solvate Substances 0.000 claims description 4
- KKTRUMAPENRITH-UHFFFAOYSA-N tert-butyl 2-[2-[3-chloro-4-(2-methylbenzoyl)anilino]phenyl]ethyl carbonate Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1CCOC(=O)OC(C)(C)C KKTRUMAPENRITH-UHFFFAOYSA-N 0.000 claims description 4
- KTWGOKKSCUEMKS-JLHYYAGUSA-N (e)-3-[2-[3-chloro-4-(2-methylbenzoyl)anilino]phenyl]prop-2-enoic acid Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1\C=C\C(O)=O KTWGOKKSCUEMKS-JLHYYAGUSA-N 0.000 claims description 3
- RFNPZCSRTULLJK-DHZHZOJOSA-N 1-[(e)-3-[2-[3-chloro-4-(2-methylbenzoyl)anilino]phenyl]prop-2-enyl]-3-ethylurea Chemical compound CCNC(=O)NC\C=C\C1=CC=CC=C1NC(C=C1Cl)=CC=C1C(=O)C1=CC=CC=C1C RFNPZCSRTULLJK-DHZHZOJOSA-N 0.000 claims description 3
- QUTJEJGGKZLXMV-UHFFFAOYSA-N 1-[2-[[5-bromo-2-[3-chloro-4-(2-methylbenzoyl)anilino]phenyl]methoxy]ethyl]imidazolidine-2,4,5-trione Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=C(Br)C=C1COCCN1C(=O)C(=O)NC1=O QUTJEJGGKZLXMV-UHFFFAOYSA-N 0.000 claims description 3
- FEPBWGFYSIXPHS-UHFFFAOYSA-N 3-[2-[2-[3-chloro-4-(2-methylbenzoyl)anilino]phenyl]ethyl]-1-methylimidazolidine-2,4-dione Chemical compound O=C1N(C)CC(=O)N1CCC1=CC=CC=C1NC(C=C1Cl)=CC=C1C(=O)C1=CC=CC=C1C FEPBWGFYSIXPHS-UHFFFAOYSA-N 0.000 claims description 3
- LXSQYLFYLSVYHI-UHFFFAOYSA-N 3-[2-[[5-bromo-2-[3-chloro-4-(2-methylbenzoyl)anilino]phenyl]methoxy]ethyl]-1-methylimidazolidine-2,4-dione Chemical compound O=C1N(C)CC(=O)N1CCOCC1=CC(Br)=CC=C1NC(C=C1Cl)=CC=C1C(=O)C1=CC=CC=C1C LXSQYLFYLSVYHI-UHFFFAOYSA-N 0.000 claims description 3
- DHMQDGOQFOQNFH-UHFFFAOYSA-M Aminoacetate Chemical compound NCC([O-])=O DHMQDGOQFOQNFH-UHFFFAOYSA-M 0.000 claims description 3
- NTOZLMJJFHITTN-RMKNXTFCSA-N [2-chloro-4-[2-[(e)-3-(2,3-dihydroxypropoxy)prop-1-enyl]anilino]phenyl]-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1\C=C\COCC(O)CO NTOZLMJJFHITTN-RMKNXTFCSA-N 0.000 claims description 3
- UTVKSMGDMZRRBR-DHZHZOJOSA-N [2-chloro-4-[2-[(e)-3-[(2,2-dimethyl-1,3-dioxolan-4-yl)methoxy]prop-1-enyl]anilino]phenyl]-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1\C=C\COCC1OC(C)(C)OC1 UTVKSMGDMZRRBR-DHZHZOJOSA-N 0.000 claims description 3
- RCCQNKHHDLILAT-UHFFFAOYSA-N [2-chloro-4-[2-[2-(3-morpholin-4-ylpropylamino)ethyl]anilino]phenyl]-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1CCNCCCN1CCOCC1 RCCQNKHHDLILAT-UHFFFAOYSA-N 0.000 claims description 3
- ZYWGKZMKBOUKDL-UHFFFAOYSA-N [2-chloro-4-[2-[2-(oxan-2-yloxy)ethoxymethyl]anilino]phenyl]-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1COCCOC1OCCCC1 ZYWGKZMKBOUKDL-UHFFFAOYSA-N 0.000 claims description 3
- WVEAJVSHVDREKJ-UHFFFAOYSA-N [2-chloro-4-[2-[2-(oxan-2-yloxy)ethyl]anilino]phenyl]-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1CCOC1OCCCC1 WVEAJVSHVDREKJ-UHFFFAOYSA-N 0.000 claims description 3
- RKZMCLZKKWICRJ-UHFFFAOYSA-N [2-chloro-4-[2-[2-[2-(2-hydroxyethoxy)ethoxy]ethoxymethyl]anilino]phenyl]-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1COCCOCCOCCO RKZMCLZKKWICRJ-UHFFFAOYSA-N 0.000 claims description 3
- HEIWFPMTWKROQV-UHFFFAOYSA-N [2-chloro-4-[2-[2-[2-[2-(oxan-2-yloxy)ethoxy]ethoxy]ethoxymethyl]anilino]phenyl]-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1COCCOCCOCCOC1OCCCC1 HEIWFPMTWKROQV-UHFFFAOYSA-N 0.000 claims description 3
- CPTGOZQAFRERIV-UHFFFAOYSA-N [2-chloro-4-[2-[2-[methyl(oxolan-2-ylmethyl)amino]ethyl]anilino]phenyl]-(2-methylphenyl)methanone Chemical compound C1CCOC1CN(C)CCC1=CC=CC=C1NC(C=C1Cl)=CC=C1C(=O)C1=CC=CC=C1C CPTGOZQAFRERIV-UHFFFAOYSA-N 0.000 claims description 3
- 229940007550 benzyl acetate Drugs 0.000 claims description 3
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 3
- QUKGYYKBILRGFE-UHFFFAOYSA-N benzyloxyacetoaldehyde Natural products CC(=O)OCC1=CC=CC=C1 QUKGYYKBILRGFE-UHFFFAOYSA-N 0.000 claims description 3
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 claims description 3
- FKRCODPIKNYEAC-UHFFFAOYSA-N propionic acid ethyl ester Natural products CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 claims description 3
- 229940090181 propyl acetate Drugs 0.000 claims description 3
- MSNYPHBTGPIMNJ-UHFFFAOYSA-N 6-chloro-4-[2-[2-(hydroxymethyl)anilino]phenyl]-6-methylcyclohexa-2,4-diene-1-carbaldehyde Chemical compound ClC1(C(C=CC(=C1)C1=C(C=CC=C1)NC1=C(C=CC=C1)CO)C=O)C MSNYPHBTGPIMNJ-UHFFFAOYSA-N 0.000 claims description 2
- YCGVIPPYKJOKMZ-UHFFFAOYSA-N BrC=1C=CC(=C(COCCOCCOCCC2=CC=C(C=C2)C)C1)NC1=CC(=C(C=C1)C(=O)C1=C(C=CC=C1)C)Cl Chemical compound BrC=1C=CC(=C(COCCOCCOCCC2=CC=C(C=C2)C)C1)NC1=CC(=C(C=C1)C(=O)C1=C(C=CC=C1)C)Cl YCGVIPPYKJOKMZ-UHFFFAOYSA-N 0.000 claims description 2
- SHZIWNPUGXLXDT-UHFFFAOYSA-N caproic acid ethyl ester Natural products CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 claims description 2
- VDEJJAPWKNTANO-DHZHZOJOSA-N ethyl 4-[[(e)-3-[2-[3-chloro-4-(2-methylbenzoyl)anilino]phenyl]prop-2-enyl]amino]-4-oxobutanoate Chemical compound CCOC(=O)CCC(=O)NC\C=C\C1=CC=CC=C1NC(C=C1Cl)=CC=C1C(=O)C1=CC=CC=C1C VDEJJAPWKNTANO-DHZHZOJOSA-N 0.000 claims description 2
- GATNOFPXSDHULC-UHFFFAOYSA-N ethylphosphonic acid Chemical compound CCP(O)(O)=O GATNOFPXSDHULC-UHFFFAOYSA-N 0.000 claims description 2
- MJVQXHCLJPERKH-DHZHZOJOSA-N n-[(e)-3-[2-[3-chloro-4-(2-methylbenzoyl)anilino]phenyl]prop-2-enyl]-n',n'-dimethylbutanediamide Chemical compound CN(C)C(=O)CCC(=O)NC\C=C\C1=CC=CC=C1NC(C=C1Cl)=CC=C1C(=O)C1=CC=CC=C1C MJVQXHCLJPERKH-DHZHZOJOSA-N 0.000 claims description 2
- VRZVPALEJCLXPR-UHFFFAOYSA-N ethyl 4-methylbenzenesulfonate Chemical compound CCOS(=O)(=O)C1=CC=C(C)C=C1 VRZVPALEJCLXPR-UHFFFAOYSA-N 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 649
- 238000002360 preparation method Methods 0.000 abstract description 127
- 238000004519 manufacturing process Methods 0.000 abstract description 46
- 238000000034 method Methods 0.000 abstract description 35
- 239000000825 pharmaceutical preparation Substances 0.000 abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 269
- 235000019439 ethyl acetate Nutrition 0.000 description 193
- 238000005481 NMR spectroscopy Methods 0.000 description 138
- 238000003818 flash chromatography Methods 0.000 description 135
- 239000003208 petroleum Substances 0.000 description 124
- 238000006243 chemical reaction Methods 0.000 description 119
- 239000000203 mixture Substances 0.000 description 103
- 239000012043 crude product Substances 0.000 description 100
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 99
- 239000003921 oil Substances 0.000 description 92
- 235000019198 oils Nutrition 0.000 description 91
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 89
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 88
- 125000001424 substituent group Chemical group 0.000 description 79
- 239000000243 solution Substances 0.000 description 73
- 239000011541 reaction mixture Substances 0.000 description 69
- 238000010626 work up procedure Methods 0.000 description 60
- 239000003480 eluent Substances 0.000 description 57
- 239000012074 organic phase Substances 0.000 description 57
- 238000000746 purification Methods 0.000 description 57
- 125000000753 cycloalkyl group Chemical group 0.000 description 54
- 150000001336 alkenes Chemical group 0.000 description 49
- 125000000217 alkyl group Chemical group 0.000 description 41
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 40
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 38
- 239000008346 aqueous phase Substances 0.000 description 35
- 239000012267 brine Substances 0.000 description 33
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 33
- 229910052739 hydrogen Inorganic materials 0.000 description 32
- 239000001257 hydrogen Substances 0.000 description 32
- 125000000623 heterocyclic group Chemical group 0.000 description 31
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 30
- 239000007858 starting material Substances 0.000 description 30
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 26
- 238000009472 formulation Methods 0.000 description 26
- 229910052736 halogen Inorganic materials 0.000 description 26
- 150000002367 halogens Chemical class 0.000 description 26
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 24
- 229910000080 stannane Inorganic materials 0.000 description 24
- 239000006188 syrup Substances 0.000 description 24
- 235000020357 syrup Nutrition 0.000 description 24
- KXCAEQNNTZANTK-UHFFFAOYSA-N stannane Chemical compound [SnH4] KXCAEQNNTZANTK-UHFFFAOYSA-N 0.000 description 23
- 238000004587 chromatography analysis Methods 0.000 description 22
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 21
- 239000007787 solid Substances 0.000 description 21
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 20
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 20
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 20
- 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 19
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 19
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 17
- 150000001412 amines Chemical class 0.000 description 17
- 150000002431 hydrogen Chemical class 0.000 description 17
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 description 16
- 239000012300 argon atmosphere Substances 0.000 description 16
- MUALRAIOVNYAIW-UHFFFAOYSA-N binap Chemical group C1=CC=CC=C1P(C=1C(=C2C=CC=CC2=CC=1)C=1C2=CC=CC=C2C=CC=1P(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 MUALRAIOVNYAIW-UHFFFAOYSA-N 0.000 description 16
- 239000007788 liquid Substances 0.000 description 16
- 238000003786 synthesis reaction Methods 0.000 description 16
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 description 15
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- 229910000104 sodium hydride Inorganic materials 0.000 description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 14
- 239000004480 active ingredient Substances 0.000 description 14
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 14
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 14
- 238000003756 stirring Methods 0.000 description 14
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 13
- 125000004093 cyano group Chemical group *C#N 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 125000000304 alkynyl group Chemical group 0.000 description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 12
- 229920006395 saturated elastomer Polymers 0.000 description 12
- 239000000725 suspension Substances 0.000 description 12
- 238000005859 coupling reaction Methods 0.000 description 11
- 239000006260 foam Substances 0.000 description 11
- 239000011734 sodium Substances 0.000 description 11
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 10
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 9
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 150000002430 hydrocarbons Chemical group 0.000 description 9
- OSDBJMYIUDLIRI-UHFFFAOYSA-N oxo-[[1-[[4-[[4-(oxoazaniumylmethylidene)pyridin-1-yl]methoxy]cyclohexyl]oxymethyl]pyridin-4-ylidene]methyl]azanium;dichloride Chemical compound [Cl-].[Cl-].C1=CC(=C[NH+]=O)C=CN1COC1CCC(OCN2C=CC(=C[NH+]=O)C=C2)CC1 OSDBJMYIUDLIRI-UHFFFAOYSA-N 0.000 description 9
- 230000008569 process Effects 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 125000004455 (C1-C3) alkylthio group Chemical group 0.000 description 8
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 description 8
- 239000012230 colorless oil Substances 0.000 description 8
- 125000002950 monocyclic group Chemical group 0.000 description 8
- 230000035484 reaction time Effects 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 8
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 description 7
- 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 7
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 7
- 125000004414 alkyl thio group Chemical group 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- LXCYSACZTOKNNS-UHFFFAOYSA-N diethoxy(oxo)phosphanium Chemical compound CCO[P+](=O)OCC LXCYSACZTOKNNS-UHFFFAOYSA-N 0.000 description 7
- 239000003814 drug Substances 0.000 description 7
- 125000000524 functional group Chemical group 0.000 description 7
- 235000002639 sodium chloride Nutrition 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 6
- LZSYGJNFCREHMD-UHFFFAOYSA-N 1-bromo-2-(bromomethyl)benzene Chemical compound BrCC1=CC=CC=C1Br LZSYGJNFCREHMD-UHFFFAOYSA-N 0.000 description 6
- ADLOWZRDUHSVRU-UHFFFAOYSA-N 2-(2-bromophenyl)ethanol Chemical compound OCCC1=CC=CC=C1Br ADLOWZRDUHSVRU-UHFFFAOYSA-N 0.000 description 6
- QBRNLAUOCDJULY-UHFFFAOYSA-N 3-[2-(2-bromophenyl)ethyl]-1-methylimidazolidine-2,4-dione Chemical compound O=C1N(C)CC(=O)N1CCC1=CC=CC=C1Br QBRNLAUOCDJULY-UHFFFAOYSA-N 0.000 description 6
- BMTZEAOGFDXDAD-UHFFFAOYSA-M 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholin-4-ium;chloride Chemical compound [Cl-].COC1=NC(OC)=NC([N+]2(C)CCOCC2)=N1 BMTZEAOGFDXDAD-UHFFFAOYSA-M 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 6
- 235000019502 Orange oil Nutrition 0.000 description 6
- 108060008682 Tumor Necrosis Factor Proteins 0.000 description 6
- 102000000852 Tumor Necrosis Factor-alpha Human genes 0.000 description 6
- 125000004429 atom Chemical group 0.000 description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 6
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 6
- 230000008878 coupling Effects 0.000 description 6
- 238000010168 coupling process Methods 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 239000004615 ingredient Substances 0.000 description 6
- 239000010502 orange oil Substances 0.000 description 6
- 229910052760 oxygen Inorganic materials 0.000 description 6
- 238000012746 preparative thin layer chromatography Methods 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- GDBLXQFNGOONMT-UHFFFAOYSA-N (2-bromophenyl)methoxy-tri(propan-2-yl)silane Chemical compound CC(C)[Si](C(C)C)(C(C)C)OCC1=CC=CC=C1Br GDBLXQFNGOONMT-UHFFFAOYSA-N 0.000 description 5
- IKLQNZZRLFIPKC-UHFFFAOYSA-N (2-chloro-4-iodophenyl)-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C1=CC=C(I)C=C1Cl IKLQNZZRLFIPKC-UHFFFAOYSA-N 0.000 description 5
- HTDJKBUTENCLRE-UHFFFAOYSA-N 1-(2-bromophenyl)propan-2-yl acetate Chemical compound CC(=O)OC(C)CC1=CC=CC=C1Br HTDJKBUTENCLRE-UHFFFAOYSA-N 0.000 description 5
- FNPMAXCCWNJYRO-UHFFFAOYSA-N 1-[2-(2-bromophenyl)ethyl]piperidine-2,6-dione Chemical compound BrC1=CC=CC=C1CCN1C(=O)CCCC1=O FNPMAXCCWNJYRO-UHFFFAOYSA-N 0.000 description 5
- SUYLYNLOCLSXRU-UHFFFAOYSA-N 1-bromo-2-(3,3,3-trifluoropropoxymethyl)benzene Chemical compound FC(F)(F)CCOCC1=CC=CC=C1Br SUYLYNLOCLSXRU-UHFFFAOYSA-N 0.000 description 5
- ABSBIARFNWSHTL-UHFFFAOYSA-N 1-bromo-2-(3-iodopropoxymethyl)benzene Chemical compound BrC1=CC=CC=C1COCCCI ABSBIARFNWSHTL-UHFFFAOYSA-N 0.000 description 5
- RWEBPSCLTNESOS-UHFFFAOYSA-N 2-[2-[(2-bromophenyl)methoxy]ethoxy]ethanol Chemical compound OCCOCCOCC1=CC=CC=C1Br RWEBPSCLTNESOS-UHFFFAOYSA-N 0.000 description 5
- UGGHCFIFWKUPSD-UHFFFAOYSA-N 2-[2-[(2-bromophenyl)methoxy]ethoxy]oxane Chemical compound BrC1=CC=CC=C1COCCOC1OCCCC1 UGGHCFIFWKUPSD-UHFFFAOYSA-N 0.000 description 5
- JVORXZAIQILLFU-UHFFFAOYSA-N 2-[2-[2-[(2-bromophenyl)methoxy]ethoxy]ethoxy]ethanol Chemical compound OCCOCCOCCOCC1=CC=CC=C1Br JVORXZAIQILLFU-UHFFFAOYSA-N 0.000 description 5
- RTRGWVFVPVHUFF-UHFFFAOYSA-N 2-[2-[2-[(2-bromophenyl)methoxy]ethoxy]ethoxy]oxane Chemical compound BrC1=CC=CC=C1COCCOCCOC1OCCCC1 RTRGWVFVPVHUFF-UHFFFAOYSA-N 0.000 description 5
- KZFSNARGVLBBLD-UHFFFAOYSA-N 2-[2-[2-[2-[(2-bromophenyl)methoxy]ethoxy]ethoxy]ethoxy]oxane Chemical compound BrC1=CC=CC=C1COCCOCCOCCOC1OCCCC1 KZFSNARGVLBBLD-UHFFFAOYSA-N 0.000 description 5
- WQIDZTIJGGRBJP-UHFFFAOYSA-N 2-[3-[(2-bromophenyl)methoxy]propoxy]oxane Chemical compound BrC1=CC=CC=C1COCCCOC1OCCCC1 WQIDZTIJGGRBJP-UHFFFAOYSA-N 0.000 description 5
- NOJRJATVXQSDGS-UHFFFAOYSA-N 2-methyl-4-tributylstannylbut-3-en-2-ol Chemical compound CCCC[Sn](CCCC)(CCCC)\C=C\C(C)(C)O NOJRJATVXQSDGS-UHFFFAOYSA-N 0.000 description 5
- WVPHKQNEWIKGIW-UHFFFAOYSA-N 3-[2-(2-bromophenyl)ethyl]-5,5-dimethyl-1,3-oxazolidine-2,4-dione Chemical compound O=C1C(C)(C)OC(=O)N1CCC1=CC=CC=C1Br WVPHKQNEWIKGIW-UHFFFAOYSA-N 0.000 description 5
- RQIOTTTVFSVFRD-UHFFFAOYSA-N 3-bromoprop-1-enyl(tributyl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)\C=C\CBr RQIOTTTVFSVFRD-UHFFFAOYSA-N 0.000 description 5
- UCAATGZZUVKWAV-UHFFFAOYSA-N 4-[2-(2-bromophenyl)ethyl]morpholine-3,5-dione Chemical compound BrC1=CC=CC=C1CCN1C(=O)COCC1=O UCAATGZZUVKWAV-UHFFFAOYSA-N 0.000 description 5
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 5
- BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 125000003282 alkyl amino group Chemical group 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 239000003153 chemical reaction reagent Substances 0.000 description 5
- ZCASAULLWDFLBH-ZIDOSWBXSA-N dimethyl 2-[(e)-3-tributylstannylprop-1-enyl]propanedioate Chemical compound CCCC[Sn](CCCC)(CCCC)C\C=C\C(C(=O)OC)C(=O)OC ZCASAULLWDFLBH-ZIDOSWBXSA-N 0.000 description 5
- 229940079593 drug Drugs 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 5
- NSETWVJZUWGCKE-UHFFFAOYSA-N propylphosphonic acid Chemical compound CCCP(O)(O)=O NSETWVJZUWGCKE-UHFFFAOYSA-N 0.000 description 5
- YHBFZZYZAWWNHP-CQSZACIVSA-N tert-butyl (4r)-4-[2-(2-aminophenyl)ethyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate Chemical compound C1OC(C)(C)N(C(=O)OC(C)(C)C)[C@@H]1CCC1=CC=CC=C1N YHBFZZYZAWWNHP-CQSZACIVSA-N 0.000 description 5
- BTVBMGYDQAYPQI-XMMPIXPASA-N tert-butyl (4r)-4-[2-[2-[3-chloro-4-(2-methylbenzoyl)anilino]phenyl]ethyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1CC[C@H]1N(C(=O)OC(C)(C)C)C(C)(C)OC1 BTVBMGYDQAYPQI-XMMPIXPASA-N 0.000 description 5
- CKMJMLQAJILELX-UHFFFAOYSA-N tert-butyl n-[2-(2-bromophenyl)ethyl]-n-methylcarbamate Chemical compound CC(C)(C)OC(=O)N(C)CCC1=CC=CC=C1Br CKMJMLQAJILELX-UHFFFAOYSA-N 0.000 description 5
- XDDHDVJHUXTTJK-UHFFFAOYSA-N 2-[[2-[3-chloro-4-(2-methylbenzoyl)anilino]phenyl]methoxy]ethyl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OCCOCC1=CC=CC=C1NC(C=C1Cl)=CC=C1C(=O)C1=CC=CC=C1C XDDHDVJHUXTTJK-UHFFFAOYSA-N 0.000 description 4
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 4
- PJEMEGHTTFJSTQ-UHFFFAOYSA-N 3-[(2-bromophenyl)methoxy]propan-1-ol Chemical compound OCCCOCC1=CC=CC=C1Br PJEMEGHTTFJSTQ-UHFFFAOYSA-N 0.000 description 4
- HRDJRILDJWUGPM-UHFFFAOYSA-N 4-[2-[3-chloro-4-(2-methylbenzoyl)anilino]anilino]-4-oxobutanoic acid Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1NC(=O)CCC(O)=O HRDJRILDJWUGPM-UHFFFAOYSA-N 0.000 description 4
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- RSXSNXMTQSJMRC-UHFFFAOYSA-N [2-chloro-4-[2-[tri(propan-2-yl)silyloxymethyl]anilino]phenyl]-(2-methylphenyl)methanone Chemical compound CC(C)[Si](C(C)C)(C(C)C)OCC1=CC=CC=C1NC(C=C1Cl)=CC=C1C(=O)C1=CC=CC=C1C RSXSNXMTQSJMRC-UHFFFAOYSA-N 0.000 description 4
- 230000009471 action Effects 0.000 description 4
- 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 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 239000012298 atmosphere Substances 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 4
- 201000010099 disease Diseases 0.000 description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
- 239000012634 fragment Substances 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- 229910052740 iodine Inorganic materials 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 239000008194 pharmaceutical composition Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000012312 sodium hydride Substances 0.000 description 4
- 239000003826 tablet Substances 0.000 description 4
- DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 4
- 230000000699 topical effect Effects 0.000 description 4
- 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 description 3
- 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 description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 3
- GJQCBCRCLGMKLQ-UHFFFAOYSA-N 1-bromo-2-(2-iodoethyl)benzene Chemical compound BrC1=CC=CC=C1CCI GJQCBCRCLGMKLQ-UHFFFAOYSA-N 0.000 description 3
- HOSRNZRYSLDCGZ-UHFFFAOYSA-N 1-bromo-2-(diethoxyphosphorylmethyl)benzene Chemical compound CCOP(=O)(OCC)CC1=CC=CC=C1Br HOSRNZRYSLDCGZ-UHFFFAOYSA-N 0.000 description 3
- QJKZCWWFBYCGPK-UHFFFAOYSA-N 2-(2-bromophenyl)ethyl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OCCC1=CC=CC=C1Br QJKZCWWFBYCGPK-UHFFFAOYSA-N 0.000 description 3
- QZVRGOQYKYFZGD-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethyl 4-[2-[3-chloro-4-(2-methylbenzoyl)anilino]anilino]-4-oxobutanoate Chemical compound COCCOCCOC(=O)CCC(=O)NC1=CC=CC=C1NC(C=C1Cl)=CC=C1C(=O)C1=CC=CC=C1C QZVRGOQYKYFZGD-UHFFFAOYSA-N 0.000 description 3
- RHPLYFZTWLENEV-UHFFFAOYSA-N 2-[(2-bromophenyl)methoxy]ethanol Chemical compound OCCOCC1=CC=CC=C1Br RHPLYFZTWLENEV-UHFFFAOYSA-N 0.000 description 3
- QKLBSIUUGLLJIS-UHFFFAOYSA-N 2-[(2-bromophenyl)methyl]isoindole-1,3-dione Chemical compound BrC1=CC=CC=C1CN1C(=O)C2=CC=CC=C2C1=O QKLBSIUUGLLJIS-UHFFFAOYSA-N 0.000 description 3
- QDSFNOHWQKVVEB-UHFFFAOYSA-N 4-(diethoxyphosphorylmethyl)morpholine Chemical compound CCOP(=O)(OCC)CN1CCOCC1 QDSFNOHWQKVVEB-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 201000004624 Dermatitis Diseases 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 102000003777 Interleukin-1 beta Human genes 0.000 description 3
- 108090000193 Interleukin-1 beta Proteins 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- 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 3
- RHYBFKMFHLPQPH-UHFFFAOYSA-N N-methylhydantoin Chemical compound CN1CC(=O)NC1=O RHYBFKMFHLPQPH-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- PVYCUEDTOJBESW-UHFFFAOYSA-N [2-chloro-4-[2-(difluoromethyl)anilino]phenyl]-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1C(F)F PVYCUEDTOJBESW-UHFFFAOYSA-N 0.000 description 3
- QFWGASILDIXGKQ-UHFFFAOYSA-N [2-chloro-4-[2-(hydroxymethyl)anilino]phenyl]-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1CO QFWGASILDIXGKQ-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 150000001450 anions Chemical class 0.000 description 3
- 229910052786 argon Inorganic materials 0.000 description 3
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 3
- KWEDUNSJJZVRKR-UHFFFAOYSA-N carbononitridic azide Chemical compound [N-]=[N+]=NC#N KWEDUNSJJZVRKR-UHFFFAOYSA-N 0.000 description 3
- 239000003795 chemical substances by application Substances 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
- 239000013078 crystal Substances 0.000 description 3
- FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 3
- FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 125000001072 heteroaryl group Chemical group 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 238000000338 in vitro Methods 0.000 description 3
- 239000012442 inert solvent Substances 0.000 description 3
- 239000003446 ligand Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 229920000609 methyl cellulose Polymers 0.000 description 3
- 239000001923 methylcellulose Substances 0.000 description 3
- 235000010981 methylcellulose Nutrition 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000002674 ointment Substances 0.000 description 3
- 238000007911 parenteral administration Methods 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 230000028327 secretion Effects 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- 125000005208 trialkylammonium group Chemical group 0.000 description 3
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 2
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 description 2
- 125000006526 (C1-C2) alkyl group Chemical group 0.000 description 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 2
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 description 2
- 125000006593 (C2-C3) alkynyl group Chemical group 0.000 description 2
- CXCHEKCRJQRVNG-UHFFFAOYSA-N 2,2,2-trifluoroethanesulfonyl chloride Chemical compound FC(F)(F)CS(Cl)(=O)=O CXCHEKCRJQRVNG-UHFFFAOYSA-N 0.000 description 2
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 2
- 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 2
- VDHOISRRKGNEJQ-UHFFFAOYSA-N 2-[[5-bromo-2-[3-chloro-4-(2-methylbenzoyl)anilino]phenyl]methoxy]ethyl 2-diethoxyphosphorylacetate Chemical compound CCOP(=O)(OCC)CC(=O)OCCOCC1=CC(Br)=CC=C1NC(C=C1Cl)=CC=C1C(=O)C1=CC=CC=C1C VDHOISRRKGNEJQ-UHFFFAOYSA-N 0.000 description 2
- 125000006280 2-bromobenzyl group Chemical group [H]C1=C([H])C(Br)=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- CEBKHWWANWSNTI-UHFFFAOYSA-N 2-methylbut-3-yn-2-ol Chemical compound CC(C)(O)C#C CEBKHWWANWSNTI-UHFFFAOYSA-N 0.000 description 2
- 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 2
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 2
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- NAOMHJUHDHXTPR-UHFFFAOYSA-N 4-[5-bromo-2-[3-chloro-4-(2-methylbenzoyl)anilino]anilino]-4-oxobutanoic acid Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=C(Br)C=C1NC(=O)CCC(O)=O NAOMHJUHDHXTPR-UHFFFAOYSA-N 0.000 description 2
- JOOXCMJARBKPKM-UHFFFAOYSA-N 4-oxopentanoic acid Chemical compound CC(=O)CCC(O)=O JOOXCMJARBKPKM-UHFFFAOYSA-N 0.000 description 2
- SUTWPJHCRAITLU-UHFFFAOYSA-N 6-aminohexan-1-ol Chemical compound NCCCCCCO SUTWPJHCRAITLU-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 244000215068 Acacia senegal Species 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 241000416162 Astragalus gummifer Species 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 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 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 102000004127 Cytokines Human genes 0.000 description 2
- 108090000695 Cytokines Proteins 0.000 description 2
- RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 2
- 206010012438 Dermatitis atopic Diseases 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical group O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
- 229920000084 Gum arabic Polymers 0.000 description 2
- 206010061218 Inflammation Diseases 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 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 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 108010003541 Platelet Activating Factor Proteins 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- 201000004681 Psoriasis Diseases 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 229920001615 Tragacanth Polymers 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- RYXZOQOZERSHHQ-UHFFFAOYSA-N [2-(2-diphenylphosphanylphenoxy)phenyl]-diphenylphosphane Chemical compound C=1C=CC=C(P(C=2C=CC=CC=2)C=2C=CC=CC=2)C=1OC1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RYXZOQOZERSHHQ-UHFFFAOYSA-N 0.000 description 2
- HDCLCHNAEZNGNV-UHFFFAOYSA-N [4-(2-amino-4-bromoanilino)-2-chlorophenyl]-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=C(Br)C=C1N HDCLCHNAEZNGNV-UHFFFAOYSA-N 0.000 description 2
- 235000010489 acacia gum Nutrition 0.000 description 2
- 239000000205 acacia gum Substances 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 239000002168 alkylating agent Substances 0.000 description 2
- 229940100198 alkylating agent Drugs 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 230000003110 anti-inflammatory effect Effects 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 208000006673 asthma Diseases 0.000 description 2
- 201000008937 atopic dermatitis Diseases 0.000 description 2
- 125000000852 azido group Chemical group *N=[N+]=[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
- 230000004071 biological effect Effects 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
- 125000001246 bromo group Chemical group Br* 0.000 description 2
- IYYIVELXUANFED-UHFFFAOYSA-N bromo(trimethyl)silane Chemical compound C[Si](C)(C)Br IYYIVELXUANFED-UHFFFAOYSA-N 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- KQIADDMXRMTWHZ-UHFFFAOYSA-N chloro-tri(propan-2-yl)silane Chemical compound CC(C)[Si](Cl)(C(C)C)C(C)C KQIADDMXRMTWHZ-UHFFFAOYSA-N 0.000 description 2
- 239000006071 cream Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 239000006196 drop Substances 0.000 description 2
- 239000003937 drug carrier Substances 0.000 description 2
- 238000009509 drug development Methods 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical compound C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- 239000008273 gelatin Substances 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 235000011852 gelatine desserts Nutrition 0.000 description 2
- 238000007429 general method Methods 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 150000004677 hydrates Chemical class 0.000 description 2
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 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
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 2
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 2
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 2
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 2
- 238000001727 in vivo 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
- 208000027866 inflammatory disease Diseases 0.000 description 2
- 230000004054 inflammatory process Effects 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000006210 lotion Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- MXAJVDHGJCYEKL-UHFFFAOYSA-N morpholine-3,5-dione Chemical compound O=C1COCC(=O)N1 MXAJVDHGJCYEKL-UHFFFAOYSA-N 0.000 description 2
- 238000000465 moulding Methods 0.000 description 2
- 230000000269 nucleophilic effect Effects 0.000 description 2
- YNOGYQAEJGADFJ-UHFFFAOYSA-N oxolan-2-ylmethanamine Chemical compound NCC1CCCO1 YNOGYQAEJGADFJ-UHFFFAOYSA-N 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 230000008506 pathogenesis Effects 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxyacetic acid Chemical compound OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-N 0.000 description 2
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 206010039073 rheumatoid arthritis Diseases 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 2
- 239000011593 sulfur Chemical group 0.000 description 2
- 238000013268 sustained release Methods 0.000 description 2
- 239000012730 sustained-release form Substances 0.000 description 2
- 238000001308 synthesis method Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 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
- 235000010487 tragacanth Nutrition 0.000 description 2
- 239000000196 tragacanth Substances 0.000 description 2
- 229940116362 tragacanth Drugs 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- DDCKIHPFCVUFLD-UHFFFAOYSA-N tributyl(3-morpholin-4-ylprop-1-enyl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)\C=C\CN1CCOCC1 DDCKIHPFCVUFLD-UHFFFAOYSA-N 0.000 description 2
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 2
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 2
- 239000003981 vehicle Substances 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- CXNIUSPIQKWYAI-UHFFFAOYSA-N xantphos Chemical compound C=12OC3=C(P(C=4C=CC=CC=4)C=4C=CC=CC=4)C=CC=C3C(C)(C)C2=CC=CC=1P(C=1C=CC=CC=1)C1=CC=CC=C1 CXNIUSPIQKWYAI-UHFFFAOYSA-N 0.000 description 2
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 1
- VCGRFBXVSFAGGA-UHFFFAOYSA-N (1,1-dioxo-1,4-thiazinan-4-yl)-[6-[[3-(4-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]methoxy]pyridin-3-yl]methanone Chemical compound CC=1ON=C(C=2C=CC(F)=CC=2)C=1COC(N=C1)=CC=C1C(=O)N1CCS(=O)(=O)CC1 VCGRFBXVSFAGGA-UHFFFAOYSA-N 0.000 description 1
- HXOYWCSTHVTLOW-UHFFFAOYSA-N (2,2-dimethyl-1,3-dioxolan-4-yl)methanamine Chemical compound CC1(C)OCC(CN)O1 HXOYWCSTHVTLOW-UHFFFAOYSA-N 0.000 description 1
- IOWGHQGLUMEZKG-UHFFFAOYSA-N (2-bromophenyl)methanol Chemical compound OCC1=CC=CC=C1Br IOWGHQGLUMEZKG-UHFFFAOYSA-N 0.000 description 1
- HZDNNJABYXNPPV-UHFFFAOYSA-N (2-chloro-2-oxoethyl) acetate Chemical compound CC(=O)OCC(Cl)=O HZDNNJABYXNPPV-UHFFFAOYSA-N 0.000 description 1
- RBGSANDHIIMIOV-UHFFFAOYSA-M (2-nitrophenyl)methyl-triphenylphosphanium;chloride Chemical compound [Cl-].[O-][N+](=O)C1=CC=CC=C1C[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 RBGSANDHIIMIOV-UHFFFAOYSA-M 0.000 description 1
- FHOAKXBXYSJBGX-YFKPBYRVSA-N (2s)-3-hydroxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid Chemical compound CC(C)(C)OC(=O)N[C@@H](CO)C(O)=O FHOAKXBXYSJBGX-YFKPBYRVSA-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
- DOIVUUCRTWRYDG-UPHRSURJSA-N (2z)-2-(2,5-dioxoimidazolidin-4-ylidene)acetic acid Chemical compound OC(=O)\C=C1/NC(=O)NC1=O DOIVUUCRTWRYDG-UPHRSURJSA-N 0.000 description 1
- OQANPHBRHBJGNZ-FYJGNVAPSA-N (3e)-6-oxo-3-[[4-(pyridin-2-ylsulfamoyl)phenyl]hydrazinylidene]cyclohexa-1,4-diene-1-carboxylic acid Chemical compound C1=CC(=O)C(C(=O)O)=C\C1=N\NC1=CC=C(S(=O)(=O)NC=2N=CC=CC=2)C=C1 OQANPHBRHBJGNZ-FYJGNVAPSA-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
- 125000006652 (C3-C12) cycloalkyl group Chemical group 0.000 description 1
- XBVNSAUITMDMLJ-UHFFFAOYSA-N (e)-3-tributylstannylprop-2-en-1-amine Chemical compound CCCC[Sn](CCCC)(CCCC)\C=C\CN XBVNSAUITMDMLJ-UHFFFAOYSA-N 0.000 description 1
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 1
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 1
- RJKPOWPTZRARKB-UHFFFAOYSA-N 1-(2-bromophenyl)propan-2-ol Chemical compound CC(O)CC1=CC=CC=C1Br RJKPOWPTZRARKB-UHFFFAOYSA-N 0.000 description 1
- BMEMBBFDTYHTLH-UHFFFAOYSA-N 1-(2-methoxyethyl)piperazine Chemical compound COCCN1CCNCC1 BMEMBBFDTYHTLH-UHFFFAOYSA-N 0.000 description 1
- HJORCZCMNWLHMB-UHFFFAOYSA-N 1-(3-aminopropyl)pyrrolidin-2-one Chemical compound NCCCN1CCCC1=O HJORCZCMNWLHMB-UHFFFAOYSA-N 0.000 description 1
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 1
- VHEICCMNYWNFQX-UHFFFAOYSA-N 1-bromo-2-(difluoromethoxy)benzene Chemical compound FC(F)OC1=CC=CC=C1Br VHEICCMNYWNFQX-UHFFFAOYSA-N 0.000 description 1
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2,2'-azo-bis-isobutyronitrile Substances N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 1
- JVSFQJZRHXAUGT-UHFFFAOYSA-N 2,2-dimethylpropanoyl chloride Chemical compound CC(C)(C)C(Cl)=O JVSFQJZRHXAUGT-UHFFFAOYSA-N 0.000 description 1
- RHZBRCQIKQUQHQ-UHFFFAOYSA-N 2-(1,3-dioxoisoindol-2-yl)acetyl chloride Chemical compound C1=CC=C2C(=O)N(CC(=O)Cl)C(=O)C2=C1 RHZBRCQIKQUQHQ-UHFFFAOYSA-N 0.000 description 1
- ZEMZPXWZVTUONV-UHFFFAOYSA-N 2-(2-dicyclohexylphosphanylphenyl)-n,n-dimethylaniline Chemical group CN(C)C1=CC=CC=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 ZEMZPXWZVTUONV-UHFFFAOYSA-N 0.000 description 1
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-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
- FFIANHVBVFPUHD-UHFFFAOYSA-N 2-[2-(2-bromophenyl)ethoxy]oxane Chemical compound BrC1=CC=CC=C1CCOC1OCCCC1 FFIANHVBVFPUHD-UHFFFAOYSA-N 0.000 description 1
- GGDTZOYXKIVAOI-UHFFFAOYSA-N 2-[3-(2-bromophenoxy)propoxy]oxane Chemical compound BrC1=CC=CC=C1OCCCOC1OCCCC1 GGDTZOYXKIVAOI-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
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- JRMAQQQTXDJDNC-UHFFFAOYSA-N 2-ethoxy-2-oxoacetic acid Chemical compound CCOC(=O)C(O)=O JRMAQQQTXDJDNC-UHFFFAOYSA-N 0.000 description 1
- ZFWFRTVIIMTOLY-UHFFFAOYSA-N 2-isothiocyanato-2-methylpropane Chemical compound CC(C)(C)N=C=S ZFWFRTVIIMTOLY-UHFFFAOYSA-N 0.000 description 1
- ASUDFOJKTJLAIK-UHFFFAOYSA-N 2-methoxyethanamine Chemical compound COCCN ASUDFOJKTJLAIK-UHFFFAOYSA-N 0.000 description 1
- 125000006022 2-methyl-2-propenyl group Chemical group 0.000 description 1
- YOETUEMZNOLGDB-UHFFFAOYSA-N 2-methylpropyl carbonochloridate Chemical compound CC(C)COC(Cl)=O YOETUEMZNOLGDB-UHFFFAOYSA-N 0.000 description 1
- LDSQQXKSEFZAPE-UHFFFAOYSA-N 2-piperidin-4-ylethanol Chemical compound OCCC1CCNCC1 LDSQQXKSEFZAPE-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- HDBGBTNNPRCVND-UHFFFAOYSA-N 3,3,3-trifluoropropan-1-ol Chemical compound OCCC(F)(F)F HDBGBTNNPRCVND-UHFFFAOYSA-N 0.000 description 1
- HCDMJFOHIXMBOV-UHFFFAOYSA-N 3-(2,6-difluoro-3,5-dimethoxyphenyl)-1-ethyl-8-(morpholin-4-ylmethyl)-4,7-dihydropyrrolo[4,5]pyrido[1,2-d]pyrimidin-2-one Chemical compound C=1C2=C3N(CC)C(=O)N(C=4C(=C(OC)C=C(OC)C=4F)F)CC3=CN=C2NC=1CN1CCOCC1 HCDMJFOHIXMBOV-UHFFFAOYSA-N 0.000 description 1
- BUSOTUQRURCMCM-UHFFFAOYSA-N 3-Phenoxypropionic acid Chemical compound OC(=O)CCOC1=CC=CC=C1 BUSOTUQRURCMCM-UHFFFAOYSA-N 0.000 description 1
- KQIGMPWTAHJUMN-UHFFFAOYSA-N 3-aminopropane-1,2-diol Chemical compound NCC(O)CO KQIGMPWTAHJUMN-UHFFFAOYSA-N 0.000 description 1
- KQIGMPWTAHJUMN-VKHMYHEASA-N 3-aminopropane-1,2-diol Chemical compound NC[C@H](O)CO KQIGMPWTAHJUMN-VKHMYHEASA-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
- UIKUBYKUYUSRSM-UHFFFAOYSA-N 3-morpholinopropylamine Chemical compound NCCCN1CCOCC1 UIKUBYKUYUSRSM-UHFFFAOYSA-N 0.000 description 1
- ODLVTDCSVYRSPD-UHFFFAOYSA-N 3-tributylstannylprop-2-en-1-ol Chemical compound CCCC[Sn](CCCC)(CCCC)\C=C\CO ODLVTDCSVYRSPD-UHFFFAOYSA-N 0.000 description 1
- KVCQTKNUUQOELD-UHFFFAOYSA-N 4-amino-n-[1-(3-chloro-2-fluoroanilino)-6-methylisoquinolin-5-yl]thieno[3,2-d]pyrimidine-7-carboxamide Chemical compound N=1C=CC2=C(NC(=O)C=3C4=NC=NC(N)=C4SC=3)C(C)=CC=C2C=1NC1=CC=CC(Cl)=C1F KVCQTKNUUQOELD-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
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 1
- HCFAJYNVAYBARA-UHFFFAOYSA-N 4-heptanone Chemical compound CCCC(=O)CCC HCFAJYNVAYBARA-UHFFFAOYSA-N 0.000 description 1
- RJBSTXIIQYFNPX-UHFFFAOYSA-N 4-methoxy-6-phenyl-1,3,5-triazin-2-amine Chemical compound COC1=NC(N)=NC(C=2C=CC=CC=2)=N1 RJBSTXIIQYFNPX-UHFFFAOYSA-N 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- XUOBVRURUPUPHB-UHFFFAOYSA-N 4-phenoxybutan-1-amine Chemical compound NCCCCOC1=CC=CC=C1 XUOBVRURUPUPHB-UHFFFAOYSA-N 0.000 description 1
- JYJFNDQBESEHJQ-UHFFFAOYSA-N 5,5-dimethyloxazolidine-2,4-dione Chemical compound CC1(C)OC(=O)NC1=O JYJFNDQBESEHJQ-UHFFFAOYSA-N 0.000 description 1
- NVDQWXGHTJREBS-UHFFFAOYSA-N 5-methyl-3-phenyl-1,2-oxazole-4-carbohydrazide Chemical compound NNC(=O)C1=C(C)ON=C1C1=CC=CC=C1 NVDQWXGHTJREBS-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
- FHVDTGUDJYJELY-UHFFFAOYSA-N 6-{[2-carboxy-4,5-dihydroxy-6-(phosphanyloxy)oxan-3-yl]oxy}-4,5-dihydroxy-3-phosphanyloxane-2-carboxylic acid Chemical compound O1C(C(O)=O)C(P)C(O)C(O)C1OC1C(C(O)=O)OC(OP)C(O)C1O FHVDTGUDJYJELY-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
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- CYJRNFFLTBEQSQ-UHFFFAOYSA-N 8-(3-methyl-1-benzothiophen-5-yl)-N-(4-methylsulfonylpyridin-3-yl)quinoxalin-6-amine Chemical compound CS(=O)(=O)C1=C(C=NC=C1)NC=1C=C2N=CC=NC2=C(C=1)C=1C=CC2=C(C(=CS2)C)C=1 CYJRNFFLTBEQSQ-UHFFFAOYSA-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
- 208000030507 AIDS Diseases 0.000 description 1
- 208000002874 Acne Vulgaris Diseases 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-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
- 241000894006 Bacteria Species 0.000 description 1
- 239000005711 Benzoic acid Substances 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
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical class O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 1
- 208000011231 Crohn disease Diseases 0.000 description 1
- 229920002785 Croscarmellose sodium Polymers 0.000 description 1
- RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 description 1
- 206010012442 Dermatitis contact Diseases 0.000 description 1
- 229920002307 Dextran Polymers 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
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
- 102000013138 Drug Receptors Human genes 0.000 description 1
- 108010065556 Drug Receptors Proteins 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- 201000005569 Gout Diseases 0.000 description 1
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 1
- 206010020751 Hypersensitivity Diseases 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 208000022559 Inflammatory bowel disease Diseases 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 102000043136 MAP kinase family Human genes 0.000 description 1
- 108091054455 MAP kinase family Proteins 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 241001529936 Murinae Species 0.000 description 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
- AYCPARAPKDAOEN-LJQANCHMSA-N N-[(1S)-2-(dimethylamino)-1-phenylethyl]-6,6-dimethyl-3-[(2-methyl-4-thieno[3,2-d]pyrimidinyl)amino]-1,4-dihydropyrrolo[3,4-c]pyrazole-5-carboxamide Chemical compound C1([C@H](NC(=O)N2C(C=3NN=C(NC=4C=5SC=CC=5N=C(C)N=4)C=3C2)(C)C)CN(C)C)=CC=CC=C1 AYCPARAPKDAOEN-LJQANCHMSA-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
- 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
- 229910021605 Palladium(II) bromide Inorganic materials 0.000 description 1
- UULYVBBLIYLRCU-UHFFFAOYSA-N Palmitinsaeure-n-tetradecylester Natural products CCCCCCCCCCCCCCCC(=O)OCCCCCCCCCCCCCC UULYVBBLIYLRCU-UHFFFAOYSA-N 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 206010040070 Septic Shock Diseases 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- BCKXLBQYZLBQEK-KVVVOXFISA-M Sodium oleate Chemical compound [Na+].CCCCCCCC\C=C/CCCCCCCC([O-])=O BCKXLBQYZLBQEK-KVVVOXFISA-M 0.000 description 1
- 229920002125 Sokalan® Polymers 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
- OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 1
- 206010046851 Uveitis Diseases 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
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-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
- BOPHLQJBICPEMU-OLQVQODUSA-N [(3s,4r)-4-acetyloxy-2,5-dioxopyrrolidin-3-yl] acetate Chemical compound CC(=O)O[C@H]1[C@@H](OC(C)=O)C(=O)NC1=O BOPHLQJBICPEMU-OLQVQODUSA-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
- 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
- VJHCJDRQFCCTHL-UHFFFAOYSA-N acetic acid 2,3,4,5,6-pentahydroxyhexanal Chemical compound CC(O)=O.OCC(O)C(O)C(O)C(O)C=O VJHCJDRQFCCTHL-UHFFFAOYSA-N 0.000 description 1
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 206010000496 acne Diseases 0.000 description 1
- 150000001263 acyl chlorides Chemical class 0.000 description 1
- 239000000464 adrenergic agent Substances 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 229940072056 alginate Drugs 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 150000001345 alkine derivatives Chemical class 0.000 description 1
- 230000007815 allergy Effects 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 238000005576 amination reaction Methods 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 230000003092 anti-cytokine Effects 0.000 description 1
- 239000003529 anticholesteremic agent Substances 0.000 description 1
- 229940127226 anticholesterol agent Drugs 0.000 description 1
- 229940065524 anticholinergics inhalants for obstructive airway diseases Drugs 0.000 description 1
- 229940125715 antihistaminic agent Drugs 0.000 description 1
- 239000000739 antihistaminic agent Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 238000003491 array Methods 0.000 description 1
- 206010003246 arthritis Diseases 0.000 description 1
- 150000001502 aryl halides Chemical class 0.000 description 1
- 239000003637 basic solution Substances 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 150000008366 benzophenones Chemical class 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 229920002988 biodegradable polymer Polymers 0.000 description 1
- 239000004621 biodegradable polymer Substances 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000008366 buffered solution 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
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 1
- 229910000024 caesium carbonate Inorganic materials 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 229960001631 carbomer Drugs 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 229940105329 carboxymethylcellulose Drugs 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 239000000812 cholinergic antagonist Substances 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- 239000003240 coconut oil Substances 0.000 description 1
- 235000019864 coconut oil Nutrition 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000007891 compressed tablet Substances 0.000 description 1
- 208000010247 contact dermatitis Diseases 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 239000002385 cottonseed oil Substances 0.000 description 1
- 229940111134 coxibs Drugs 0.000 description 1
- 229960005168 croscarmellose Drugs 0.000 description 1
- 229960000913 crospovidone Drugs 0.000 description 1
- 239000001767 crosslinked sodium carboxy methyl cellulose Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 150000001925 cycloalkenes Chemical group 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- KQWGXHWJMSMDJJ-UHFFFAOYSA-N cyclohexyl isocyanate Chemical compound O=C=NC1CCCCC1 KQWGXHWJMSMDJJ-UHFFFAOYSA-N 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 239000003255 cyclooxygenase 2 inhibitor Substances 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 230000016396 cytokine production Effects 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- BEPAFCGSDWSTEL-UHFFFAOYSA-N dimethyl malonate Chemical compound COC(=O)CC(=O)OC BEPAFCGSDWSTEL-UHFFFAOYSA-N 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- CNXMDTWQWLGCPE-UHFFFAOYSA-N ditert-butyl-(2-phenylphenyl)phosphane Chemical group CC(C)(C)P(C(C)(C)C)C1=CC=CC=C1C1=CC=CC=C1 CNXMDTWQWLGCPE-UHFFFAOYSA-N 0.000 description 1
- 230000003828 downregulation Effects 0.000 description 1
- 230000036267 drug metabolism Effects 0.000 description 1
- 230000004064 dysfunction Effects 0.000 description 1
- 239000008157 edible vegetable oil Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 1
- DUVOZUPPHBRJJO-UHFFFAOYSA-N ethyl 2-isocyanatoacetate Chemical compound CCOC(=O)CN=C=O DUVOZUPPHBRJJO-UHFFFAOYSA-N 0.000 description 1
- WUDNUHPRLBTKOJ-UHFFFAOYSA-N ethyl isocyanate Chemical compound CCN=C=O WUDNUHPRLBTKOJ-UHFFFAOYSA-N 0.000 description 1
- UAYKGOMDUQLCJS-UHFFFAOYSA-N ethylsulfanyl acetate Chemical compound CCSOC(C)=O UAYKGOMDUQLCJS-UHFFFAOYSA-N 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 230000009969 flowable effect Effects 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
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 239000003862 glucocorticoid Substances 0.000 description 1
- 239000000174 gluconic acid Substances 0.000 description 1
- 235000012208 gluconic acid Nutrition 0.000 description 1
- 229950006191 gluconic acid Drugs 0.000 description 1
- 235000001727 glucose Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- PKHMTIRCAFTBDS-UHFFFAOYSA-N hexanoyl hexanoate Chemical compound CCCCCC(=O)OC(=O)CCCCC PKHMTIRCAFTBDS-UHFFFAOYSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 description 1
- 229940091173 hydantoin Drugs 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 229960000890 hydrocortisone Drugs 0.000 description 1
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 1
- 239000008172 hydrogenated vegetable oil Substances 0.000 description 1
- 229940071870 hydroiodic acid Drugs 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 1
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 1
- 229960000905 indomethacin Drugs 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 230000000266 injurious effect Effects 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 150000004694 iodide salts Chemical class 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000000865 liniment Substances 0.000 description 1
- 239000002502 liposome Substances 0.000 description 1
- 239000012669 liquid formulation Substances 0.000 description 1
- 150000002641 lithium Chemical class 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000008176 lyophilized powder Substances 0.000 description 1
- 150000002680 magnesium Chemical class 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 235000019359 magnesium stearate Nutrition 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
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- RBQRWNWVPQDTJJ-UHFFFAOYSA-N methacryloyloxyethyl isocyanate Chemical compound CC(=C)C(=O)OCCN=C=O RBQRWNWVPQDTJJ-UHFFFAOYSA-N 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- WSFSSNUMVMOOMR-BJUDXGSMSA-N methanone Chemical compound O=[11CH2] WSFSSNUMVMOOMR-BJUDXGSMSA-N 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 150000005217 methyl ethers Chemical class 0.000 description 1
- ZPJZSEHCMJYUPI-UHFFFAOYSA-N methyl piperazine-1-carboxylate Chemical compound COC(=O)N1CCNCC1 ZPJZSEHCMJYUPI-UHFFFAOYSA-N 0.000 description 1
- 229960002900 methylcellulose Drugs 0.000 description 1
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- DILRJUIACXKSQE-UHFFFAOYSA-N n',n'-dimethylethane-1,2-diamine Chemical compound CN(C)CCN DILRJUIACXKSQE-UHFFFAOYSA-N 0.000 description 1
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-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
- VJUDVVHGQMPPEI-UHFFFAOYSA-N n-methyl-1-(oxolan-2-yl)methanamine Chemical compound CNCC1CCCO1 VJUDVVHGQMPPEI-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 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
- 229960002009 naproxen Drugs 0.000 description 1
- 229920001206 natural gum Polymers 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000007764 o/w emulsion Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 150000002941 palladium compounds Chemical class 0.000 description 1
- MUJIDPITZJWBSW-UHFFFAOYSA-N palladium(2+) Chemical group [Pd+2] MUJIDPITZJWBSW-UHFFFAOYSA-N 0.000 description 1
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- INIOZDBICVTGEO-UHFFFAOYSA-L palladium(ii) bromide Chemical compound Br[Pd]Br INIOZDBICVTGEO-UHFFFAOYSA-L 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- ZFLIKDUSUDBGCD-UHFFFAOYSA-N parabanic acid Chemical compound O=C1NC(=O)C(=O)N1 ZFLIKDUSUDBGCD-UHFFFAOYSA-N 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 229960001639 penicillamine Drugs 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 239000008024 pharmaceutical diluent Substances 0.000 description 1
- 238000005191 phase separation Methods 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
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 1
- 230000003711 photoprotective effect Effects 0.000 description 1
- KNCYXPMJDCCGSJ-UHFFFAOYSA-N piperidine-2,6-dione Chemical compound O=C1CCCC(=O)N1 KNCYXPMJDCCGSJ-UHFFFAOYSA-N 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229940068968 polysorbate 80 Drugs 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 235000013809 polyvinylpolypyrrolidone Nutrition 0.000 description 1
- 229920000523 polyvinylpolypyrrolidone Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- FYRHIOVKTDQVFC-UHFFFAOYSA-M potassium phthalimide Chemical compound [K+].C1=CC=C2C(=O)[N-]C(=O)C2=C1 FYRHIOVKTDQVFC-UHFFFAOYSA-M 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 229940002612 prodrug Drugs 0.000 description 1
- 239000000651 prodrug Substances 0.000 description 1
- 230000002062 proliferating effect Effects 0.000 description 1
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 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
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000000306 recurrent effect Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 150000004492 retinoid derivatives Chemical class 0.000 description 1
- 229960001860 salicylate Drugs 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000036303 septic shock Effects 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
- XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
- 208000017520 skin disease Diseases 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229940083542 sodium Drugs 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 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
- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 1
- SDKPSXWGRWWLKR-UHFFFAOYSA-M sodium;9,10-dioxoanthracene-1-sulfonate Chemical compound [Na+].O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2S(=O)(=O)[O-] SDKPSXWGRWWLKR-UHFFFAOYSA-M 0.000 description 1
- RNVYQYLELCKWAN-UHFFFAOYSA-N solketal Chemical compound CC1(C)OCC(CO)O1 RNVYQYLELCKWAN-UHFFFAOYSA-N 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 201000005671 spondyloarthropathy Diseases 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 229940071117 starch glycolate Drugs 0.000 description 1
- 239000003206 sterilizing agent Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- 229960001940 sulfasalazine Drugs 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 229940037128 systemic glucocorticoids Drugs 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 229960001367 tartaric acid Drugs 0.000 description 1
- PNJXYVJNOCLJLJ-MRVPVSSYSA-N tert-butyl (4s)-4-formyl-2,2-dimethyl-1,3-oxazolidine-3-carboxylate Chemical compound CC(C)(C)OC(=O)N1[C@H](C=O)COC1(C)C PNJXYVJNOCLJLJ-MRVPVSSYSA-N 0.000 description 1
- VJEHAGIRIFQFGS-UHFFFAOYSA-N tert-butyl [[cyano(phenyl)methyl]amino] carbonate Chemical compound CC(C)(C)OC(=O)ONC(C#N)C1=CC=CC=C1 VJEHAGIRIFQFGS-UHFFFAOYSA-N 0.000 description 1
- LPRGKTMWGYRTPG-VSOVPVGVSA-N tert-butyl n-[(2r)-1-[[(e)-3-[2-[3-chloro-4-(2-methylbenzoyl)anilino]phenyl]prop-2-enyl]amino]-3-hydroxy-1-oxopropan-2-yl]carbamate Chemical compound CC1=CC=CC=C1C(=O)C(C(=C1)Cl)=CC=C1NC1=CC=CC=C1\C=C\CNC(=O)[C@@H](CO)NC(=O)OC(C)(C)C LPRGKTMWGYRTPG-VSOVPVGVSA-N 0.000 description 1
- CCLKBQZVNSHZLO-UHFFFAOYSA-N tert-butyl n-[2-(2-bromophenyl)ethyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCC1=CC=CC=C1Br CCLKBQZVNSHZLO-UHFFFAOYSA-N 0.000 description 1
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 125000003507 tetrahydrothiofenyl group Chemical group 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- DBGVGMSCBYYSLD-UHFFFAOYSA-N tributylstannane Chemical compound CCCC[SnH](CCCC)CCCC DBGVGMSCBYYSLD-UHFFFAOYSA-N 0.000 description 1
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- BPLUKJNHPBNVQL-UHFFFAOYSA-N triphenylarsine Chemical compound C1=CC=CC=C1[As](C=1C=CC=CC=1)C1=CC=CC=C1 BPLUKJNHPBNVQL-UHFFFAOYSA-N 0.000 description 1
- UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 description 1
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-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
- 239000007762 w/o emulsion Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
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
- C07C225/02—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 acyclic carbon atoms of the carbon skeleton
- C07C225/14—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 acyclic carbon atoms of the carbon skeleton the carbon skeleton being unsaturated
- C07C225/16—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 acyclic carbon atoms of the carbon skeleton the carbon skeleton being unsaturated and containing six-membered aromatic rings
-
- 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
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- 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
- A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
-
- 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
- A61P17/00—Drugs for dermatological disorders
- A61P17/10—Anti-acne agents
-
- 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
- A61P19/00—Drugs for skeletal disorders
- A61P19/06—Antigout agents, e.g. antihyperuricemic or uricosuric agents
-
- 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
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- 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
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/40—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino groups bound to carbon atoms of at least one six-membered aromatic ring and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/44—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino groups bound to carbon atoms of at least one six-membered aromatic ring and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton with carboxyl groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by unsaturated carbon chains
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/34—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups
- C07C233/35—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
- C07C233/40—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to an acyclic carbon atom of a carbon skeleton containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/34—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups
- C07C233/42—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring
- C07C233/43—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of a saturated carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C235/10—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated having the nitrogen atom of at least one of the carboxamide groups bound to an acyclic carbon atom of a hydrocarbon radical substituted by nitrogen atoms not being part of nitro or nitroso groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C235/18—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated having at least one of the singly-bound oxygen atoms further bound to a carbon atom of a six-membered aromatic ring, e.g. phenoxyacetamides
- C07C235/20—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated having at least one of the singly-bound oxygen atoms further bound to a carbon atom of a six-membered aromatic ring, e.g. phenoxyacetamides having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/70—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/72—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton with the carbon atoms of the carboxamide groups bound to acyclic carbon atoms
- C07C235/74—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton with the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of a saturated carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C271/20—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by nitrogen atoms not being part of nitro or nitroso groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C271/22—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/63—Esters of sulfonic acids
- C07C309/72—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C309/73—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of non-condensed six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/01—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms
- C07C311/02—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C311/09—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton the carbon skeleton being further substituted by at least two halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/44—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
- C07C317/48—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton the carbon skeleton being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
- C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/52—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/263—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms
- C07D207/27—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/36—Oxygen or sulfur atoms
- C07D207/40—2,5-Pyrrolidine-diones
- C07D207/404—2,5-Pyrrolidine-diones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. succinimide
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/72—Two oxygen atoms, e.g. hydantoin
- C07D233/74—Two oxygen atoms, e.g. hydantoin with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to other ring members
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/135—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/10—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/14—Radicals substituted by nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D309/10—Oxygen atoms
- C07D309/12—Oxygen atoms only hydrogen atoms and one oxygen atom directly attached to ring carbon atoms, e.g. tetrahydropyranyl ethers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/18—Radicals substituted by singly bound oxygen or sulfur atoms
- C07D317/22—Radicals substituted by singly bound oxygen or sulfur atoms etherified
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/28—Radicals substituted by nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/12—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains three hetero rings
- C07D493/14—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Rheumatology (AREA)
- Physical Education & Sports Medicine (AREA)
- Dermatology (AREA)
- Pulmonology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Virology (AREA)
- Pain & Pain Management (AREA)
- Immunology (AREA)
- Heart & Thoracic Surgery (AREA)
- Vascular Medicine (AREA)
- Molecular Biology (AREA)
- Tropical Medicine & Parasitology (AREA)
- AIDS & HIV (AREA)
- Urology & Nephrology (AREA)
- Ophthalmology & Optometry (AREA)
- Cardiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Furan Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Saccharide Compounds (AREA)
- Pyrrole Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US31502501P | 2001-08-28 | 2001-08-28 | |
| DKPA200200189 | 2002-02-08 | ||
| PCT/DK2002/000557 WO2003018535A2 (en) | 2001-08-28 | 2002-08-26 | Novel aminobenzoephenones |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010089290A Division JP2010189410A (ja) | 2001-08-28 | 2010-04-08 | 新規アミノベンゾフェノン |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2005500400A JP2005500400A (ja) | 2005-01-06 |
| JP2005500400A5 JP2005500400A5 (https=) | 2006-01-05 |
| JP4540984B2 true JP4540984B2 (ja) | 2010-09-08 |
Family
ID=26069134
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003523200A Expired - Fee Related JP4540984B2 (ja) | 2001-08-28 | 2002-08-26 | 新規アミノベンゾフェノン |
| JP2010089290A Pending JP2010189410A (ja) | 2001-08-28 | 2010-04-08 | 新規アミノベンゾフェノン |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010089290A Pending JP2010189410A (ja) | 2001-08-28 | 2010-04-08 | 新規アミノベンゾフェノン |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US7034015B2 (https=) |
| EP (1) | EP1423356A2 (https=) |
| JP (2) | JP4540984B2 (https=) |
| KR (1) | KR100896667B1 (https=) |
| CN (1) | CN100347151C (https=) |
| AU (1) | AU2002331310B2 (https=) |
| BR (1) | BR0212249A (https=) |
| CA (1) | CA2458611C (https=) |
| HU (1) | HUP0401644A3 (https=) |
| IL (2) | IL160442A0 (https=) |
| MX (1) | MXPA04001912A (https=) |
| PL (1) | PL207487B1 (https=) |
| RU (1) | RU2361855C2 (https=) |
| WO (1) | WO2003018535A2 (https=) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2010189410A (ja) * | 2001-08-28 | 2010-09-02 | Leo Pharma As | 新規アミノベンゾフェノン |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7129229B2 (en) * | 2000-08-11 | 2006-10-31 | Nanogen Recognomics Gmbh | Hydrazide building blocks and hydrazide modified biomolecules |
| 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 |
| KR101260236B1 (ko) | 2004-12-13 | 2013-05-06 | 레오 파마 에이/에스 | 트리아졸 치환된 아미노벤조페논 화합물 |
| DE102005022020A1 (de) * | 2005-05-12 | 2006-11-23 | Merckle Gmbh | Dibenzocycloheptanverbindungen und pharmazeutische Mittel, welche diese Verbindungen enthalten |
| EP2206534A1 (de) | 2008-10-09 | 2010-07-14 | c-a-i-r biosciences GmbH | Dibenzocycloheptanonderivate und pharmazeutische Mittel, welche diese Verbindungen enthalten |
| AU2010301449B2 (en) * | 2009-09-30 | 2013-03-14 | Toray Industries, Inc. | 2,3-dihydro-1H-indene-2-ylurea derivative and pharmaceutical application of same |
| KR102098606B1 (ko) * | 2012-10-31 | 2020-04-09 | 후지필름 도야마 케미컬 가부시키가이샤 | 신규 아민 유도체 또는 그 염 |
| US9758445B2 (en) * | 2013-04-09 | 2017-09-12 | Materia, Inc. | Preparation of surfactants via cross-metathesis |
| WO2015126462A1 (en) * | 2014-02-19 | 2015-08-27 | Materia, Inc. | Preparation of surfactants via cross-metathesis |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57177058A (en) | 1981-04-24 | 1982-10-30 | Hodogaya Chem Co Ltd | Novel fluoran compound |
| EP0859771A4 (en) * | 1995-10-31 | 2000-03-15 | Merck & Co Inc | SUBSTITUTED PYRIDYLPYRROLE, PREPARATIONS CONTAINING SUCH COMPOUNDS AND METHOD FOR THE USE THEREOF |
| GB9701453D0 (en) * | 1997-01-24 | 1997-03-12 | Leo Pharm Prod Ltd | Aminobenzophenones |
| JPH11349568A (ja) * | 1998-06-08 | 1999-12-21 | Maruho Co Ltd | ラクタム誘導体及びその医薬用途 |
| RU2240995C2 (ru) * | 1999-07-16 | 2004-11-27 | Лео Фармасьютикал Продактс Лтд.А/С (Левенс Кемиске Фабрик Продукционсактиесельскаб) | Аминобензофеноны в качестве ингибиторов интерлейкина il-1бета и фактора некроза опухолей tnf-альфа |
| EP1210325B1 (en) * | 1999-07-16 | 2004-10-06 | Leo Pharma A/S | Aminobenzophenones as inhibitors of il-1beta and tnf-alpha |
| ES2228555T3 (es) * | 1999-07-16 | 2005-04-16 | Leo Pharma A/S | Aminobenzofenonas con inhibidores de la il-1beta y tnf-alfa. |
| AU768473B2 (en) | 1999-07-16 | 2003-12-11 | Leo Pharmaceutical Products Ltd. A/S (Lovens Kemiske Fabrik Produktionsaktieselskab) | Novel aminobenzophenones |
| ATE277889T1 (de) | 1999-07-16 | 2004-10-15 | Leo Pharma As | Aminobenzophenone als inhibitoren von il-1beta und tnf-alpha |
| MXPA02005604A (es) * | 1999-12-06 | 2004-09-10 | Leo Pharma As | Aminobenzofenonas como inhibidores de il-1beta y tnf-alfa. |
| AU2001260081B2 (en) * | 2000-05-22 | 2005-07-28 | Leo Pharma A/S | Benzophenones as inhibitors of il-1beta and tnf-alpha |
| US20020165286A1 (en) * | 2000-12-08 | 2002-11-07 | Hanne Hedeman | Dermal anti-inflammatory composition |
| KR100896667B1 (ko) * | 2001-08-28 | 2009-05-14 | 레오 파마 에이/에스 | 신규한 아미노벤조페논 및 이를 포함하는 약제학적 조성물 |
-
2002
- 2002-08-26 KR KR1020047003014A patent/KR100896667B1/ko not_active Expired - Fee Related
- 2002-08-26 JP JP2003523200A patent/JP4540984B2/ja not_active Expired - Fee Related
- 2002-08-26 IL IL16044202A patent/IL160442A0/xx unknown
- 2002-08-26 PL PL368686A patent/PL207487B1/pl not_active IP Right Cessation
- 2002-08-26 CN CNB028193571A patent/CN100347151C/zh not_active Expired - Fee Related
- 2002-08-26 MX MXPA04001912A patent/MXPA04001912A/es active IP Right Grant
- 2002-08-26 AU AU2002331310A patent/AU2002331310B2/en not_active Ceased
- 2002-08-26 EP EP02767145A patent/EP1423356A2/en not_active Withdrawn
- 2002-08-26 WO PCT/DK2002/000557 patent/WO2003018535A2/en not_active Ceased
- 2002-08-26 HU HU0401644A patent/HUP0401644A3/hu unknown
- 2002-08-26 RU RU2004109142/04A patent/RU2361855C2/ru not_active IP Right Cessation
- 2002-08-26 BR BR0212249-9A patent/BR0212249A/pt active Search and Examination
- 2002-08-26 CA CA2458611A patent/CA2458611C/en not_active Expired - Fee Related
- 2002-08-28 US US10/228,954 patent/US7034015B2/en not_active Expired - Fee Related
-
2004
- 2004-02-17 IL IL160442A patent/IL160442A/en not_active IP Right Cessation
-
2010
- 2010-04-08 JP JP2010089290A patent/JP2010189410A/ja active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2010189410A (ja) * | 2001-08-28 | 2010-09-02 | Leo Pharma As | 新規アミノベンゾフェノン |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2005500400A (ja) | 2005-01-06 |
| IL160442A0 (en) | 2004-07-25 |
| CA2458611A1 (en) | 2003-03-06 |
| CA2458611C (en) | 2012-05-29 |
| IL160442A (en) | 2011-11-30 |
| MXPA04001912A (es) | 2004-07-23 |
| WO2003018535A3 (en) | 2004-03-18 |
| HUP0401644A2 (hu) | 2004-11-29 |
| US7034015B2 (en) | 2006-04-25 |
| PL207487B1 (pl) | 2010-12-31 |
| KR20040029455A (ko) | 2004-04-06 |
| BR0212249A (pt) | 2004-10-05 |
| WO2003018535A2 (en) | 2003-03-06 |
| CN100347151C (zh) | 2007-11-07 |
| KR100896667B1 (ko) | 2009-05-14 |
| AU2002331310B2 (en) | 2008-07-17 |
| PL368686A1 (en) | 2005-04-04 |
| JP2010189410A (ja) | 2010-09-02 |
| RU2361855C2 (ru) | 2009-07-20 |
| EP1423356A2 (en) | 2004-06-02 |
| RU2004109142A (ru) | 2005-08-20 |
| US20030119902A1 (en) | 2003-06-26 |
| HK1068606A1 (zh) | 2005-04-29 |
| HUP0401644A3 (en) | 2008-03-28 |
| CN1561327A (zh) | 2005-01-05 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2010189410A (ja) | 新規アミノベンゾフェノン | |
| US7550481B2 (en) | Phenylamide and pyridylamide beta-secretase inhibitors for the treatment of Alzheimer's disease | |
| US6555710B1 (en) | Aminobenzophenones as inhibitors of IL-1 β and TNF-α | |
| TWI709562B (zh) | 吡咯并〔2,3-d〕嘧啶化合物的製造方法與中間產物及其用途 | |
| CN102036956A (zh) | 取代的吡咯烷和哌啶化合物、它们的衍生物、以及用于治疗疼痛的方法 | |
| JP2021534215A (ja) | 病的症状の治療における使用のための芳香族分子 | |
| PL206246B1 (pl) | Pochodna hydroksynorefedryny, jej kryształy, kompozycja farmaceutyczna, lek oraz zastosowanie | |
| WO2023115002A1 (en) | Analogs of 4-bromo-2,5-dimethoxyphenethylamine | |
| CN114269747B (zh) | 一种1’,2’-二氢-3’h-螺[环丁烷1,4’-异喹啉]-3’-酮衍生物及其应用 | |
| AU2002331310A1 (en) | Novel aminobenzoephenones | |
| RU2335490C2 (ru) | Соединения карбоновой кислоты, фармацевтическая композиция на их основе, способ лечения и применение | |
| JP7807487B2 (ja) | 新規の芳香族化合物 | |
| CN111433185A (zh) | 钾离子及trpv1通道的调节剂及其用途 | |
| JP2021534212A (ja) | 病的状態の治療における使用のための芳香族分子 | |
| US12486231B2 (en) | Targeted nitroxide compounds and their use in treating ferroptosis-related diseases | |
| RU2780482C2 (ru) | СПОСОБ ПОЛУЧЕНИЯ И ПРОМЕЖУТОЧНЫЕ ПРОДУКТЫ ДЛЯ ПОЛУЧЕНИЯ ПИРРОЛО[2,3-d]ПИРИМИДИНА И ЕГО ПРИМЕНЕНИЕ | |
| JP2006510688A (ja) | 新規アミノベンゾフェノン化合物 | |
| JP4852230B2 (ja) | プロパノールアミノメチルテトラリン、それらの製造方法およびそれらを含む医薬組成物 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20050823 |
|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20050823 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20080325 |
|
| A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20080624 |
|
| A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20080701 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20080922 |
|
| A02 | Decision of refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A02 Effective date: 20091208 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20100408 |
|
| A911 | Transfer to examiner for re-examination before appeal (zenchi) |
Free format text: JAPANESE INTERMEDIATE CODE: A911 Effective date: 20100531 |
|
| TRDD | Decision of grant or rejection written | ||
| A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20100615 |
|
| A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 |
|
| A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20100623 |
|
| R150 | Certificate of patent or registration of utility model |
Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20130702 Year of fee payment: 3 |
|
| LAPS | Cancellation because of no payment of annual fees |