AU2007275743A1 - Phosphorus derivatives as histone deacetylase inhibitors - Google Patents
Phosphorus derivatives as histone deacetylase inhibitors Download PDFInfo
- Publication number
- AU2007275743A1 AU2007275743A1 AU2007275743A AU2007275743A AU2007275743A1 AU 2007275743 A1 AU2007275743 A1 AU 2007275743A1 AU 2007275743 A AU2007275743 A AU 2007275743A AU 2007275743 A AU2007275743 A AU 2007275743A AU 2007275743 A1 AU2007275743 A1 AU 2007275743A1
- Authority
- AU
- Australia
- Prior art keywords
- amino
- phenyl
- thienyl
- alkyl
- carbonyl
- 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.)
- Abandoned
Links
- 150000003017 phosphorus Chemical class 0.000 title description 31
- 239000003276 histone deacetylase inhibitor Substances 0.000 title description 26
- 229940121372 histone deacetylase inhibitor Drugs 0.000 title description 13
- -1 tetrahydro-dioxo-pyrimidinyl Chemical group 0.000 claims description 228
- 125000000217 alkyl group Chemical group 0.000 claims description 210
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 202
- 150000001875 compounds Chemical class 0.000 claims description 187
- 125000003118 aryl group Chemical group 0.000 claims description 156
- 229910052739 hydrogen Inorganic materials 0.000 claims description 143
- 125000000623 heterocyclic group Chemical group 0.000 claims description 127
- 239000001257 hydrogen Substances 0.000 claims description 127
- 125000001072 heteroaryl group Chemical group 0.000 claims description 121
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 113
- 150000002431 hydrogen Chemical class 0.000 claims description 79
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 79
- 125000005843 halogen group Chemical group 0.000 claims description 75
- 125000003282 alkyl amino group Chemical group 0.000 claims description 72
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 72
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 68
- 206010028980 Neoplasm Diseases 0.000 claims description 63
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 54
- 125000003342 alkenyl group Chemical group 0.000 claims description 50
- 125000000304 alkynyl group Chemical group 0.000 claims description 50
- 201000011510 cancer Diseases 0.000 claims description 48
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 46
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 46
- 229910052799 carbon Inorganic materials 0.000 claims description 45
- 150000003839 salts Chemical class 0.000 claims description 45
- 125000003545 alkoxy group Chemical group 0.000 claims description 42
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 38
- 125000001188 haloalkyl group Chemical group 0.000 claims description 38
- 238000011282 treatment Methods 0.000 claims description 38
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 36
- 125000005113 hydroxyalkoxy group Chemical group 0.000 claims description 36
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 36
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 35
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 34
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 34
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 33
- 239000002253 acid Substances 0.000 claims description 32
- 125000004432 carbon atom Chemical group C* 0.000 claims description 30
- 150000001408 amides Chemical class 0.000 claims description 29
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 claims description 29
- 238000002360 preparation method Methods 0.000 claims description 29
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 claims description 28
- 125000001544 thienyl group Chemical group 0.000 claims description 28
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 24
- 239000003814 drug Substances 0.000 claims description 22
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 20
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims description 19
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 17
- 125000004429 atom Chemical group 0.000 claims description 15
- BCDIWLCKOCHCIH-UHFFFAOYSA-M methylphosphinate Chemical compound CP([O-])=O BCDIWLCKOCHCIH-UHFFFAOYSA-M 0.000 claims description 14
- 229910052757 nitrogen Inorganic materials 0.000 claims description 14
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 12
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 12
- 125000004437 phosphorous atom Chemical group 0.000 claims description 12
- 230000002265 prevention Effects 0.000 claims description 12
- 125000004076 pyridyl group Chemical group 0.000 claims description 12
- 125000001153 fluoro group Chemical group F* 0.000 claims description 11
- 125000002837 carbocyclic group Chemical group 0.000 claims description 10
- MLCHBQKMVKNBOV-UHFFFAOYSA-M dioxido(phenyl)phosphanium Chemical compound [O-]P(=O)C1=CC=CC=C1 MLCHBQKMVKNBOV-UHFFFAOYSA-M 0.000 claims description 10
- 235000005152 nicotinamide Nutrition 0.000 claims description 10
- 239000011570 nicotinamide Substances 0.000 claims description 10
- 229960003966 nicotinamide Drugs 0.000 claims description 10
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 10
- 150000002148 esters Chemical class 0.000 claims description 9
- 239000008194 pharmaceutical composition Substances 0.000 claims description 9
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 8
- 229910052727 yttrium Chemical group 0.000 claims description 8
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 7
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 239000003937 drug carrier Substances 0.000 claims description 7
- 125000004970 halomethyl group Chemical group 0.000 claims description 7
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 6
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 claims description 6
- 125000002541 furyl group Chemical group 0.000 claims description 6
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 6
- 125000000335 thiazolyl group Chemical group 0.000 claims description 6
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 5
- CTWHIIYQRAXVAL-UHFFFAOYSA-N n-(2-amino-5-phenylphenyl)-4-[[ethoxy(methyl)phosphoryl]methyl]benzamide Chemical compound C1=CC(CP(C)(=O)OCC)=CC=C1C(=O)NC1=CC(C=2C=CC=CC=2)=CC=C1N CTWHIIYQRAXVAL-UHFFFAOYSA-N 0.000 claims description 5
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 5
- ZMIRFCWMDNOYEN-UHFFFAOYSA-N 1-phosphorosooxyethane Chemical compound CCOP=O ZMIRFCWMDNOYEN-UHFFFAOYSA-N 0.000 claims description 4
- 241000124008 Mammalia Species 0.000 claims description 4
- 125000005872 benzooxazolyl group Chemical group 0.000 claims description 4
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 4
- YTUZNJNHFHNOAH-UHFFFAOYSA-N n-(2-amino-5-thiophen-2-ylphenyl)-4-(diethoxyphosphorylmethyl)benzamide Chemical compound C1=CC(CP(=O)(OCC)OCC)=CC=C1C(=O)NC1=CC(C=2SC=CC=2)=CC=C1N YTUZNJNHFHNOAH-UHFFFAOYSA-N 0.000 claims description 4
- LFGREXWGYUGZLY-UHFFFAOYSA-N phosphoryl Chemical group [P]=O LFGREXWGYUGZLY-UHFFFAOYSA-N 0.000 claims description 4
- MHSKRLJMQQNJNC-UHFFFAOYSA-N terephthalamide Chemical compound NC(=O)C1=CC=C(C(N)=O)C=C1 MHSKRLJMQQNJNC-UHFFFAOYSA-N 0.000 claims description 4
- IMLZDMUDBWXUHD-UHFFFAOYSA-N [4-[(2-amino-5-thiophen-2-ylphenyl)carbamoyl]phenyl]-ethoxyphosphinic acid Chemical compound C1=CC(P(O)(=O)OCC)=CC=C1C(=O)NC1=CC(C=2SC=CC=2)=CC=C1N IMLZDMUDBWXUHD-UHFFFAOYSA-N 0.000 claims description 3
- VSUBEANUFSZOFE-UHFFFAOYSA-N dimethoxyphosphorylmethyl n-[[4-[(2-amino-5-thiophen-2-ylphenyl)carbamoyl]phenyl]methyl]carbamate Chemical compound C1=CC(CNC(=O)OCP(=O)(OC)OC)=CC=C1C(=O)NC1=CC(C=2SC=CC=2)=CC=C1N VSUBEANUFSZOFE-UHFFFAOYSA-N 0.000 claims description 3
- INAOTIRHBPFEMW-UHFFFAOYSA-N n-(2-amino-5-thiophen-2-ylphenyl)-4-diethoxyphosphorylbenzamide Chemical compound C1=CC(P(=O)(OCC)OCC)=CC=C1C(=O)NC1=CC(C=2SC=CC=2)=CC=C1N INAOTIRHBPFEMW-UHFFFAOYSA-N 0.000 claims description 3
- GGPWKPKVUDMKLK-UHFFFAOYSA-N 4-[amino(dimethoxyphosphoryl)methyl]-n-(2-amino-5-thiophen-2-ylphenyl)benzamide Chemical compound C1=CC(C(N)P(=O)(OC)OC)=CC=C1C(=O)NC1=CC(C=2SC=CC=2)=CC=C1N GGPWKPKVUDMKLK-UHFFFAOYSA-N 0.000 claims description 2
- KTEFVLGWPDOLOT-UHFFFAOYSA-N 4-n-(2-amino-5-thiophen-2-ylphenyl)-1-n-(4-diethoxyphosphorylphenyl)benzene-1,4-dicarboxamide Chemical compound C1=CC(P(=O)(OCC)OCC)=CC=C1NC(=O)C1=CC=C(C(=O)NC=2C(=CC=C(C=2)C=2SC=CC=2)N)C=C1 KTEFVLGWPDOLOT-UHFFFAOYSA-N 0.000 claims description 2
- PCEDCJBQSDAHEZ-UHFFFAOYSA-N 4-n-(2-amino-5-thiophen-2-ylphenyl)-1-n-(diethoxyphosphorylmethyl)benzene-1,4-dicarboxamide Chemical compound C1=CC(C(=O)NCP(=O)(OCC)OCC)=CC=C1C(=O)NC1=CC(C=2SC=CC=2)=CC=C1N PCEDCJBQSDAHEZ-UHFFFAOYSA-N 0.000 claims description 2
- MQSCSQCCOQPRGR-UHFFFAOYSA-N C1=CC(CCP(=O)OC)=CC=C1C(=O)NC1=CC(C=2C=CC=CC=2)=CC=C1N Chemical compound C1=CC(CCP(=O)OC)=CC=C1C(=O)NC1=CC(C=2C=CC=CC=2)=CC=C1N MQSCSQCCOQPRGR-UHFFFAOYSA-N 0.000 claims description 2
- ILENFOYXUAIPHY-UHFFFAOYSA-N C1=CC(CP(=O)OCC)=CC=C1C(=O)NC1=CC(C=2C=CC=CC=2)=CC=C1N Chemical compound C1=CC(CP(=O)OCC)=CC=C1C(=O)NC1=CC(C=2C=CC=CC=2)=CC=C1N ILENFOYXUAIPHY-UHFFFAOYSA-N 0.000 claims description 2
- HJXCBADSQFUQOI-UHFFFAOYSA-N C1=CC(CP(O)(=O)CC)=CC=C1C(=O)NC1=CC(C=2SC=CC=2)=CC=C1N Chemical compound C1=CC(CP(O)(=O)CC)=CC=C1C(=O)NC1=CC(C=2SC=CC=2)=CC=C1N HJXCBADSQFUQOI-UHFFFAOYSA-N 0.000 claims description 2
- ZVJSJXGZYNVNJJ-UHFFFAOYSA-N C1=NC(CP(=O)OCC)=CC=C1C(=O)NC1=CC(C=2SC=CC=2)=CC=C1N Chemical compound C1=NC(CP(=O)OCC)=CC=C1C(=O)NC1=CC(C=2SC=CC=2)=CC=C1N ZVJSJXGZYNVNJJ-UHFFFAOYSA-N 0.000 claims description 2
- RREXEHYADZAGNY-UHFFFAOYSA-N CC(C)C([PH2]=O)(C(C)C)c1ccc(cc1)C(=O)Nc1cc(ccc1N)-c1cccs1 Chemical compound CC(C)C([PH2]=O)(C(C)C)c1ccc(cc1)C(=O)Nc1cc(ccc1N)-c1cccs1 RREXEHYADZAGNY-UHFFFAOYSA-N 0.000 claims description 2
- CCSFZWFJHYWSQS-UHFFFAOYSA-N CCC(CC)([PH2]=O)c1ccc(cc1)C(=O)Nc1cc(ccc1N)-c1cccs1 Chemical compound CCC(CC)([PH2]=O)c1ccc(cc1)C(=O)Nc1cc(ccc1N)-c1cccs1 CCSFZWFJHYWSQS-UHFFFAOYSA-N 0.000 claims description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 2
- WUMZZJGDPOOIQV-UHFFFAOYSA-N [4-[(2-amino-5-thiophen-2-ylphenyl)carbamoyl]phenyl]methyl-methoxyphosphinic acid Chemical compound C1=CC(CP(O)(=O)OC)=CC=C1C(=O)NC1=CC(C=2SC=CC=2)=CC=C1N WUMZZJGDPOOIQV-UHFFFAOYSA-N 0.000 claims description 2
- IPWXMLMEBMYQEH-UHFFFAOYSA-N [4-[(2-amino-5-thiophen-2-ylphenyl)carbamoyl]phenyl]methyl-phenylphosphinic acid Chemical compound NC1=CC=C(C=2SC=CC=2)C=C1NC(=O)C(C=C1)=CC=C1CP(O)(=O)C1=CC=CC=C1 IPWXMLMEBMYQEH-UHFFFAOYSA-N 0.000 claims description 2
- FBHAQWFWVCBCIC-UHFFFAOYSA-N [methoxy(methyl)phosphoryl]methyl n-[[4-[(2-amino-5-thiophen-2-ylphenyl)carbamoyl]phenyl]methyl]carbamate Chemical compound C1=CC(CNC(=O)OCP(C)(=O)OC)=CC=C1C(=O)NC1=CC(C=2SC=CC=2)=CC=C1N FBHAQWFWVCBCIC-UHFFFAOYSA-N 0.000 claims description 2
- YSECCFDJGQJTOS-UHFFFAOYSA-N benzyl-dihydroxy-imino-$l^{5}-phosphane Chemical compound NP(O)(=O)CC1=CC=CC=C1 YSECCFDJGQJTOS-UHFFFAOYSA-N 0.000 claims description 2
- UBOMZDHKDUWMMT-UHFFFAOYSA-N diethoxyphosphorylmethyl n-[[4-[(2-amino-5-thiophen-2-ylphenyl)carbamoyl]phenyl]methyl]carbamate Chemical compound C1=CC(CNC(=O)OCP(=O)(OCC)OCC)=CC=C1C(=O)NC1=CC(C=2SC=CC=2)=CC=C1N UBOMZDHKDUWMMT-UHFFFAOYSA-N 0.000 claims description 2
- 125000004494 ethyl ester group Chemical group 0.000 claims description 2
- CNEYPBWQKKNLRR-UHFFFAOYSA-N methyl 2-[4-[(2-amino-5-thiophen-2-ylphenyl)carbamoyl]phenyl]-2-diethoxyphosphorylacetate Chemical compound C1=CC(C(C(=O)OC)P(=O)(OCC)OCC)=CC=C1C(=O)NC1=CC(C=2SC=CC=2)=CC=C1N CNEYPBWQKKNLRR-UHFFFAOYSA-N 0.000 claims description 2
- WAINQPQXUFDOMI-UHFFFAOYSA-N methyl n-[[4-[(2-amino-5-phenylphenyl)carbamoyl]phenyl]methyl]-n-(diethoxyphosphorylmethyl)carbamate Chemical compound C1=CC(CN(CP(=O)(OCC)OCC)C(=O)OC)=CC=C1C(=O)NC1=CC(C=2C=CC=CC=2)=CC=C1N WAINQPQXUFDOMI-UHFFFAOYSA-N 0.000 claims description 2
- WYFALBFHJSYFAO-UHFFFAOYSA-N n-(2-amino-5-phenylphenyl)-4-(dimethylphosphoryloxymethyl)benzamide Chemical compound C1=CC(COP(C)(=O)C)=CC=C1C(=O)NC1=CC(C=2C=CC=CC=2)=CC=C1N WYFALBFHJSYFAO-UHFFFAOYSA-N 0.000 claims description 2
- NCEVWOGNBOVMOF-UHFFFAOYSA-N n-(2-amino-5-phenylphenyl)-4-[(dimethoxyphosphorylamino)methyl]benzamide Chemical compound C1=CC(CNP(=O)(OC)OC)=CC=C1C(=O)NC1=CC(C=2C=CC=CC=2)=CC=C1N NCEVWOGNBOVMOF-UHFFFAOYSA-N 0.000 claims description 2
- UBDIUMNACGCCTR-UHFFFAOYSA-N n-(2-amino-5-phenylphenyl)-4-[1-fluoro-1-[methoxy(phenyl)phosphoryl]ethyl]benzamide Chemical compound C=1C=C(C(=O)NC=2C(=CC=C(C=2)C=2C=CC=CC=2)N)C=CC=1C(C)(F)P(=O)(OC)C1=CC=CC=C1 UBDIUMNACGCCTR-UHFFFAOYSA-N 0.000 claims description 2
- FLTYYPYDLAWPFP-UHFFFAOYSA-N n-(2-amino-5-phenylphenyl)-4-[dimethoxyphosphoryl(hydroxy)methyl]benzamide Chemical compound C1=CC(C(O)P(=O)(OC)OC)=CC=C1C(=O)NC1=CC(C=2C=CC=CC=2)=CC=C1N FLTYYPYDLAWPFP-UHFFFAOYSA-N 0.000 claims description 2
- CACUQOLBCPYQJI-UHFFFAOYSA-N n-(2-amino-5-phenylphenyl)-4-[methoxy(phenyl)phosphoryl]benzamide Chemical compound C=1C=C(C(=O)NC=2C(=CC=C(C=2)C=2C=CC=CC=2)N)C=CC=1P(=O)(OC)C1=CC=CC=C1 CACUQOLBCPYQJI-UHFFFAOYSA-N 0.000 claims description 2
- ZAGKNILLERWTGX-UHFFFAOYSA-N n-(2-amino-5-phenylphenyl)-4-diethoxyphosphorylbenzamide Chemical compound C1=CC(P(=O)(OCC)OCC)=CC=C1C(=O)NC1=CC(C=2C=CC=CC=2)=CC=C1N ZAGKNILLERWTGX-UHFFFAOYSA-N 0.000 claims description 2
- WQECPISOOFKNCV-UHFFFAOYSA-N n-(2-amino-5-thiophen-2-ylphenyl)-4-(1-dimethoxyphosphoryl-1-fluoroethyl)benzamide Chemical compound C1=CC(C(C)(F)P(=O)(OC)OC)=CC=C1C(=O)NC1=CC(C=2SC=CC=2)=CC=C1N WQECPISOOFKNCV-UHFFFAOYSA-N 0.000 claims description 2
- FDTXTODRFOCNDQ-UHFFFAOYSA-N n-(2-amino-5-thiophen-2-ylphenyl)-4-(1-dimethylphosphoryloxyethyl)benzamide Chemical compound C1=CC(C(OP(C)(C)=O)C)=CC=C1C(=O)NC1=CC(C=2SC=CC=2)=CC=C1N FDTXTODRFOCNDQ-UHFFFAOYSA-N 0.000 claims description 2
- QBKOGZSXDDBBFL-UHFFFAOYSA-N n-(2-amino-5-thiophen-2-ylphenyl)-4-(2-methyl-2-oxo-1,2$l^{5}-oxaphospholan-5-yl)benzamide Chemical compound O1P(C)(=O)CCC1C1=CC=C(C(=O)NC=2C(=CC=C(C=2)C=2SC=CC=2)N)C=C1 QBKOGZSXDDBBFL-UHFFFAOYSA-N 0.000 claims description 2
- PFNDDTSYOWMNCT-UHFFFAOYSA-N n-(2-amino-5-thiophen-2-ylphenyl)-4-(diethoxyphosphorylamino)benzamide Chemical compound C1=CC(NP(=O)(OCC)OCC)=CC=C1C(=O)NC1=CC(C=2SC=CC=2)=CC=C1N PFNDDTSYOWMNCT-UHFFFAOYSA-N 0.000 claims description 2
- SNZOUEFPTPSOAA-UHFFFAOYSA-N n-(2-amino-5-thiophen-2-ylphenyl)-4-[(1-methyl-4-oxo-1,4$l^{5}-azaphosphinan-4-yl)methyl]benzamide Chemical compound C1CN(C)CCP1(=O)CC1=CC=C(C(=O)NC=2C(=CC=C(C=2)C=2SC=CC=2)N)C=C1 SNZOUEFPTPSOAA-UHFFFAOYSA-N 0.000 claims description 2
- XFVNEVGARVXYRT-UHFFFAOYSA-N n-(2-amino-5-thiophen-2-ylphenyl)-4-[1-fluoro-1-[methoxy(phenyl)phosphoryl]ethyl]benzamide Chemical compound C=1C=C(C(=O)NC=2C(=CC=C(C=2)C=2SC=CC=2)N)C=CC=1C(C)(F)P(=O)(OC)C1=CC=CC=C1 XFVNEVGARVXYRT-UHFFFAOYSA-N 0.000 claims description 2
- DQTPTUFAZBCYRY-UHFFFAOYSA-N n-(2-amino-5-thiophen-2-ylphenyl)-4-[2,2-bis(diethoxyphosphoryl)ethyl]benzamide Chemical compound C1=CC(CC(P(=O)(OCC)OCC)P(=O)(OCC)OCC)=CC=C1C(=O)NC1=CC(C=2SC=CC=2)=CC=C1N DQTPTUFAZBCYRY-UHFFFAOYSA-N 0.000 claims description 2
- YYQXPHCUJQTCRY-UHFFFAOYSA-N n-(2-amino-5-thiophen-2-ylphenyl)-4-[[cyclobutyloxy(ethyl)phosphoryl]methyl]benzamide Chemical compound C1CCC1OP(=O)(CC)CC(C=C1)=CC=C1C(=O)NC(C(=CC=1)N)=CC=1C1=CC=CS1 YYQXPHCUJQTCRY-UHFFFAOYSA-N 0.000 claims description 2
- IMRLWHUCIGYDSE-UHFFFAOYSA-N n-(2-amino-5-thiophen-2-ylphenyl)-4-[[cyclobutyloxy(methyl)phosphoryl]methyl]benzamide Chemical compound C1CCC1OP(=O)(C)CC(C=C1)=CC=C1C(=O)NC(C(=CC=1)N)=CC=1C1=CC=CS1 IMRLWHUCIGYDSE-UHFFFAOYSA-N 0.000 claims description 2
- KFGDGDXWTSPQRB-UHFFFAOYSA-N n-(2-amino-5-thiophen-2-ylphenyl)-4-[[ethoxy(ethyl)phosphoryl]methyl]benzamide Chemical compound C1=CC(CP(=O)(CC)OCC)=CC=C1C(=O)NC1=CC(C=2SC=CC=2)=CC=C1N KFGDGDXWTSPQRB-UHFFFAOYSA-N 0.000 claims description 2
- YCZQPIPSISTQIP-UHFFFAOYSA-N n-(2-amino-5-thiophen-2-ylphenyl)-4-[[ethoxy(methyl)phosphoryl]methyl]benzamide Chemical compound C1=CC(CP(C)(=O)OCC)=CC=C1C(=O)NC1=CC(C=2SC=CC=2)=CC=C1N YCZQPIPSISTQIP-UHFFFAOYSA-N 0.000 claims description 2
- BQATZQQVKCHLGZ-UHFFFAOYSA-N n-(2-amino-5-thiophen-2-ylphenyl)-4-[[ethyl(methoxy)phosphoryl]methyl]benzamide Chemical compound C1=CC(CP(=O)(CC)OC)=CC=C1C(=O)NC1=CC(C=2SC=CC=2)=CC=C1N BQATZQQVKCHLGZ-UHFFFAOYSA-N 0.000 claims description 2
- CHHLSEXKCNNREI-UHFFFAOYSA-N n-(2-amino-5-thiophen-2-ylphenyl)-4-[[ethyl(propan-2-yloxy)phosphoryl]methyl]benzamide Chemical compound C1=CC(CP(=O)(CC)OC(C)C)=CC=C1C(=O)NC1=CC(C=2SC=CC=2)=CC=C1N CHHLSEXKCNNREI-UHFFFAOYSA-N 0.000 claims description 2
- BPMHDNJABBOROI-UHFFFAOYSA-N n-(2-amino-5-thiophen-2-ylphenyl)-4-[[methoxy(methyl)phosphoryl]methyl]benzamide Chemical compound C1=CC(CP(C)(=O)OC)=CC=C1C(=O)NC1=CC(C=2SC=CC=2)=CC=C1N BPMHDNJABBOROI-UHFFFAOYSA-N 0.000 claims description 2
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- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having sulfur atoms, with or without selenium or tellurium atoms, as the only ring hetero atoms
- C07F9/655345—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having sulfur atoms, with or without selenium or tellurium atoms, as the only ring hetero atoms the sulfur atom being part of a five-membered ring
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- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/50—Organo-phosphines
- C07F9/53—Organo-phosphine oxides; Organo-phosphine thioxides
- C07F9/5304—Acyclic saturated phosphine oxides or thioxides
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
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- C07F9/50—Organo-phosphines
- C07F9/53—Organo-phosphine oxides; Organo-phosphine thioxides
- C07F9/5325—Aromatic phosphine oxides or thioxides (P-C aromatic linkage)
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
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- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
- C07F9/6503—Five-membered rings
- C07F9/65031—Five-membered rings having the nitrogen atoms in the positions 1 and 2
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
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- C07F9/6558—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system
- C07F9/65586—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system at least one of the hetero rings does not contain nitrogen as ring hetero atom
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- C—CHEMISTRY; METALLURGY
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- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6571—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms
- C07F9/657154—Cyclic esteramides of oxyacids of phosphorus
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
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- C07F9/6571—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms
- C07F9/657163—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms the ring phosphorus atom being bound to at least one carbon atom
- C07F9/657181—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms the ring phosphorus atom being bound to at least one carbon atom the ring phosphorus atom and, at least, one ring oxygen atom being part of a (thio)phosphonic acid derivative
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
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- C07F9/6581—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and nitrogen atoms with or without oxygen or sulfur atoms, as ring hetero atoms
- C07F9/6584—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and nitrogen atoms with or without oxygen or sulfur atoms, as ring hetero atoms having one phosphorus atom as ring hetero atom
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- Health & Medical Sciences (AREA)
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- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
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PCT/US2007/016123 WO2008010985A2 (en) | 2006-07-20 | 2007-07-16 | Phosphorus derivatives as histone deacetylase inhibitors |
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US8017321B2 (en) | 2004-01-23 | 2011-09-13 | The Regents Of The University Of Colorado, A Body Corporate | Gefitinib sensitivity-related gene expression and products and methods related thereto |
CA2567293C (en) | 2004-05-27 | 2017-05-16 | The Regents Of The University Of Colorado | Methods for prediction of clinical outcome to epidermal growth factor receptor inhibitors by cancer patients |
AU2007221207A1 (en) | 2006-02-28 | 2007-09-07 | Merck Sharp & Dohme Corp. | Inhibitors of histone deacetylase |
CN101808518A (zh) * | 2007-06-27 | 2010-08-18 | 默沙东公司 | 作为组蛋白脱乙酰酶抑制剂的吡啶基和嘧啶基衍生物 |
US8389553B2 (en) * | 2007-06-27 | 2013-03-05 | Merck Sharp & Dohme Corp. | 4-carboxybenzylamino derivatives as histone deacetylase inhibitors |
NZ591896A (en) | 2008-08-29 | 2013-03-28 | Treventis Corp | Compositions and methods of treating amyloid disease |
US9265734B2 (en) | 2008-09-03 | 2016-02-23 | Biomarin Pharmaceutical Inc. | Compositions including 6-aminohexanoic acid derivatives as HDAC inhibitors |
EP2608672B1 (en) * | 2010-08-23 | 2020-12-16 | Syntrix Biosystems, Inc. | Aminopyridine- and aminopyrimidinecarboxamides as cxcr2 modulators |
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- 2007-07-16 WO PCT/US2007/016123 patent/WO2008010985A2/en active Application Filing
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- 2007-07-16 US US12/309,459 patent/US7981874B2/en not_active Expired - Fee Related
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US20090270351A1 (en) | 2009-10-29 |
EP2049124A4 (en) | 2010-02-10 |
JP2009544611A (ja) | 2009-12-17 |
CA2657288A1 (en) | 2008-01-24 |
EP2049124A2 (en) | 2009-04-22 |
US7981874B2 (en) | 2011-07-19 |
WO2008010985A3 (en) | 2008-04-03 |
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