JP2009544611A5 - - Google Patents
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- JP2009544611A5 JP2009544611A5 JP2009520791A JP2009520791A JP2009544611A5 JP 2009544611 A5 JP2009544611 A5 JP 2009544611A5 JP 2009520791 A JP2009520791 A JP 2009520791A JP 2009520791 A JP2009520791 A JP 2009520791A JP 2009544611 A5 JP2009544611 A5 JP 2009544611A5
- Authority
- JP
- Japan
- 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.)
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- 125000000217 alkyl group Chemical group 0.000 claims 122
- -1 tetrahydro-dioxo-pyrimidinyl Chemical group 0.000 claims 111
- 125000000623 heterocyclic group Chemical group 0.000 claims 59
- 229910052739 hydrogen Inorganic materials 0.000 claims 57
- 125000003118 aryl group Chemical group 0.000 claims 55
- 125000001072 heteroaryl group Chemical group 0.000 claims 53
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 45
- 239000001257 hydrogen Substances 0.000 claims 44
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 41
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 38
- 125000000753 cycloalkyl group Chemical group 0.000 claims 37
- 150000002431 hydrogen Chemical class 0.000 claims 30
- 125000003282 alkyl amino group Chemical group 0.000 claims 26
- 125000005843 halogen group Chemical group 0.000 claims 25
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 24
- 125000001188 haloalkyl group Chemical group 0.000 claims 21
- 229910052698 phosphorus Inorganic materials 0.000 claims 20
- 125000000304 alkynyl group Chemical group 0.000 claims 17
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 14
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims 14
- 239000011574 phosphorus Substances 0.000 claims 14
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 13
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims 13
- 125000003342 alkenyl group Chemical group 0.000 claims 13
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 13
- 125000005113 hydroxyalkoxy group Chemical group 0.000 claims 13
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 13
- 125000003545 alkoxy group Chemical group 0.000 claims 12
- 150000001875 compounds Chemical class 0.000 claims 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 12
- 150000001408 amides Chemical class 0.000 claims 10
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 10
- 125000004399 C1-C4 alkenyl group Chemical group 0.000 claims 9
- 125000004432 carbon atom Chemical group C* 0.000 claims 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims 9
- 150000003839 salts Chemical class 0.000 claims 9
- 229960003966 nicotinamide Drugs 0.000 claims 7
- 235000005152 nicotinamide Nutrition 0.000 claims 7
- 239000011570 nicotinamide Substances 0.000 claims 7
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 7
- 125000004438 haloalkoxy group Chemical group 0.000 claims 6
- 125000004437 phosphorous atom Chemical group 0.000 claims 6
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 5
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 5
- 125000006725 C1-C10 alkenyl group Chemical group 0.000 claims 4
- 125000004429 atom Chemical group 0.000 claims 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 3
- 125000001153 fluoro group Chemical group F* 0.000 claims 3
- 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 3
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 claims 3
- 125000001544 thienyl group Chemical group 0.000 claims 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 2
- 239000003937 drug carrier Substances 0.000 claims 2
- BCDIWLCKOCHCIH-UHFFFAOYSA-M methylphosphinate Chemical compound CP([O-])=O BCDIWLCKOCHCIH-UHFFFAOYSA-M 0.000 claims 2
- 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 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 2
- MHSKRLJMQQNJNC-UHFFFAOYSA-N terephthalamide Chemical compound NC(=O)C1=CC=C(C(N)=O)C=C1 MHSKRLJMQQNJNC-UHFFFAOYSA-N 0.000 claims 2
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims 1
- VMEKFWCBOQLCAL-UHFFFAOYSA-N 1-n-(2-amino-5-thiophen-2-ylphenyl)-4-n-(2-dimethylphosphorylethyl)-4-n-methylbenzene-1,4-dicarboxamide Chemical compound C1=CC(C(=O)N(CCP(C)(C)=O)C)=CC=C1C(=O)NC1=CC(C=2SC=CC=2)=CC=C1N VMEKFWCBOQLCAL-UHFFFAOYSA-N 0.000 claims 1
- CKNJMGAGZRKWKV-UHFFFAOYSA-N 1-n-(2-amino-5-thiophen-2-ylphenyl)-4-n-(2-diphenylphosphorylethyl)-4-n-methylbenzene-1,4-dicarboxamide Chemical compound C=1C=C(C(=O)NC=2C(=CC=C(C=2)C=2SC=CC=2)N)C=CC=1C(=O)N(C)CCP(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 CKNJMGAGZRKWKV-UHFFFAOYSA-N 0.000 claims 1
- ODRXYEFXGFXNPD-UHFFFAOYSA-N 1-n-(2-amino-5-thiophen-2-ylphenyl)-4-n-[2-di(propan-2-yl)phosphorylethyl]-4-n-methylbenzene-1,4-dicarboxamide Chemical compound C1=CC(C(=O)N(C)CCP(=O)(C(C)C)C(C)C)=CC=C1C(=O)NC1=CC(C=2SC=CC=2)=CC=C1N ODRXYEFXGFXNPD-UHFFFAOYSA-N 0.000 claims 1
- ZMIRFCWMDNOYEN-UHFFFAOYSA-N 1-phosphorosooxyethane Chemical compound CCOP=O ZMIRFCWMDNOYEN-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- BDDSPZNUJPSRHS-UHFFFAOYSA-N CC(C)([PH2]=O)c1ccc(cc1)C(=O)Nc1cc(ccc1N)-c1cccs1 Chemical compound CC(C)([PH2]=O)c1ccc(cc1)C(=O)Nc1cc(ccc1N)-c1cccs1 BDDSPZNUJPSRHS-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- DPTYIELSLKOASW-UHFFFAOYSA-N [1-[4-[(2-amino-5-phenylphenyl)carbamoyl]phenyl]-2-(4-dimethylphosphorylphenyl)ethyl] carbamate Chemical compound C1=CC(P(C)(=O)C)=CC=C1CC(OC(N)=O)C1=CC=C(C(=O)NC=2C(=CC=C(C=2)C=2C=CC=CC=2)N)C=C1 DPTYIELSLKOASW-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- SGTDHRDPWCCRIU-UHFFFAOYSA-N [4-[(2-amino-5-thiophen-2-ylphenyl)carbamoyl]phenyl]methyl-ethoxyphosphinic acid Chemical compound C1=CC(CP(O)(=O)OCC)=CC=C1C(=O)NC1=CC(C=2SC=CC=2)=CC=C1N SGTDHRDPWCCRIU-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- GUWDMFLFDNKNNZ-UHFFFAOYSA-N [ethoxy(phenyl)phosphoryl]oxymethylbenzene Chemical compound C=1C=CC=CC=1P(=O)(OCC)OCC1=CC=CC=C1 GUWDMFLFDNKNNZ-UHFFFAOYSA-N 0.000 claims 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims 1
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 claims 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims 1
- VFKYXFWRQLWZAI-UHFFFAOYSA-N benzyl dimethyl phosphate Chemical compound COP(=O)(OC)OCC1=CC=CC=C1 VFKYXFWRQLWZAI-UHFFFAOYSA-N 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- HRLOBRMHZBUNRV-UHFFFAOYSA-N di(propan-2-yl)phosphoryloxymethylbenzene Chemical compound CC(C)P(=O)(C(C)C)OCC1=CC=CC=C1 HRLOBRMHZBUNRV-UHFFFAOYSA-N 0.000 claims 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- DQBAITHIHYRSFA-UHFFFAOYSA-N diethylphosphoryloxymethylbenzene Chemical compound CCP(=O)(CC)OCC1=CC=CC=C1 DQBAITHIHYRSFA-UHFFFAOYSA-N 0.000 claims 1
- UOUBSNKDIDEUCV-UHFFFAOYSA-N dimethylphosphoryloxybenzene Chemical compound CP(C)(=O)OC1=CC=CC=C1 UOUBSNKDIDEUCV-UHFFFAOYSA-N 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- IHAOAEQSLBFIBH-UHFFFAOYSA-N methyl n-[[4-[(2-amino-5-phenylphenyl)carbamoyl]phenyl]methyl]-n-(2-dimethylphosphorylethyl)carbamate Chemical compound C1=CC(CN(CCP(C)(C)=O)C(=O)OC)=CC=C1C(=O)NC1=CC(C=2C=CC=CC=2)=CC=C1N IHAOAEQSLBFIBH-UHFFFAOYSA-N 0.000 claims 1
- ODGOZOATYPDTTC-UHFFFAOYSA-N n-(2-amino-5-phenylphenyl)-4-(1-dimethoxyphosphoryl-1-fluoroethyl)benzamide Chemical compound C1=CC(C(C)(F)P(=O)(OC)OC)=CC=C1C(=O)NC1=CC(C=2C=CC=CC=2)=CC=C1N ODGOZOATYPDTTC-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- UBMHIJDOAXHEOW-UHFFFAOYSA-N n-(2-amino-5-thiophen-2-ylphenyl)-4-(dimethoxyphosphorylmethyl)benzamide Chemical compound C1=CC(CP(=O)(OC)OC)=CC=C1C(=O)NC1=CC(C=2SC=CC=2)=CC=C1N UBMHIJDOAXHEOW-UHFFFAOYSA-N 0.000 claims 1
- MPSZFNFRFZNTPG-UHFFFAOYSA-N n-(2-amino-5-thiophen-2-ylphenyl)-4-(dimethylphosphoryloxymethyl)benzamide Chemical compound C1=CC(COP(C)(=O)C)=CC=C1C(=O)NC1=CC(C=2SC=CC=2)=CC=C1N MPSZFNFRFZNTPG-UHFFFAOYSA-N 0.000 claims 1
- SDFJPCASBWGULI-UHFFFAOYSA-N n-(2-amino-5-thiophen-2-ylphenyl)-4-[(diethoxyphosphorylmethylamino)methyl]benzamide Chemical compound C1=CC(CNCP(=O)(OCC)OCC)=CC=C1C(=O)NC1=CC(C=2SC=CC=2)=CC=C1N SDFJPCASBWGULI-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- QJODLYAVZJVYKS-UHFFFAOYSA-N n-(2-amino-5-thiophen-2-ylphenyl)-4-[[(benzylamino)-methoxyphosphoryl]methyl]benzamide Chemical compound C=1C=CC=CC=1CNP(=O)(OC)CC(C=C1)=CC=C1C(=O)NC(C(=CC=1)N)=CC=1C1=CC=CS1 QJODLYAVZJVYKS-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- IGXWCUCYSHXLRR-UHFFFAOYSA-N n-(2-amino-5-thiophen-2-ylphenyl)-4-[[ethoxy(phenyl)phosphoryl]-hydroxymethyl]benzamide Chemical compound C=1C=CC=CC=1P(=O)(OCC)C(O)C(C=C1)=CC=C1C(=O)NC(C(=CC=1)N)=CC=1C1=CC=CS1 IGXWCUCYSHXLRR-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- DQEIWGQMBKANNE-UHFFFAOYSA-N n-(2-amino-5-thiophen-2-ylphenyl)-4-[[ethyl-(pyridin-3-ylmethylamino)phosphoryl]methyl]benzamide Chemical compound C=1C=CN=CC=1CNP(=O)(CC)CC(C=C1)=CC=C1C(=O)NC(C(=CC=1)N)=CC=1C1=CC=CS1 DQEIWGQMBKANNE-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- MLQPEVICWDREHG-UHFFFAOYSA-N n-(2-amino-5-thiophen-2-ylphenyl)-4-[[methoxy(phenyl)phosphoryl]methyl]benzamide Chemical compound C=1C=CC=CC=1P(=O)(OC)CC(C=C1)=CC=C1C(=O)NC(C(=CC=1)N)=CC=1C1=CC=CS1 MLQPEVICWDREHG-UHFFFAOYSA-N 0.000 claims 1
- JAPPOWHVFQXLKQ-UHFFFAOYSA-N n-(2-amino-5-thiophen-2-ylphenyl)-4-[[methyl(propan-2-yloxy)phosphoryl]methyl]benzamide Chemical compound C1=CC(CP(C)(=O)OC(C)C)=CC=C1C(=O)NC1=CC(C=2SC=CC=2)=CC=C1N JAPPOWHVFQXLKQ-UHFFFAOYSA-N 0.000 claims 1
- OUFPMTVHORTIMR-UHFFFAOYSA-N n-(2-amino-5-thiophen-2-ylphenyl)-4-[[methyl-(pyridin-3-ylmethylamino)phosphoryl]methyl]benzamide Chemical compound C=1C=CN=CC=1CNP(=O)(C)CC(C=C1)=CC=C1C(=O)NC(C(=CC=1)N)=CC=1C1=CC=CS1 OUFPMTVHORTIMR-UHFFFAOYSA-N 0.000 claims 1
- OJTUFXWBIXIHGO-UHFFFAOYSA-N n-(2-amino-5-thiophen-2-ylphenyl)-4-[dimethoxyphosphoryl(fluoro)methyl]benzamide Chemical compound C1=CC(C(F)P(=O)(OC)OC)=CC=C1C(=O)NC1=CC(C=2SC=CC=2)=CC=C1N OJTUFXWBIXIHGO-UHFFFAOYSA-N 0.000 claims 1
- ZPTAFHNTDBSESF-UHFFFAOYSA-N n-(2-amino-5-thiophen-2-ylphenyl)-4-[dimethoxyphosphoryl(hydroxy)methyl]benzamide Chemical compound C1=CC(C(O)P(=O)(OC)OC)=CC=C1C(=O)NC1=CC(C=2SC=CC=2)=CC=C1N ZPTAFHNTDBSESF-UHFFFAOYSA-N 0.000 claims 1
- UAKBOEPBOPWUKA-UHFFFAOYSA-N n-(2-amino-5-thiophen-2-ylphenyl)-4-di(propan-2-yl)phosphorylbenzamide Chemical compound C1=CC(P(=O)(C(C)C)C(C)C)=CC=C1C(=O)NC1=CC(C=2SC=CC=2)=CC=C1N UAKBOEPBOPWUKA-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- UWHGTSUWTQKZAD-UHFFFAOYSA-N n-(2-amino-5-thiophen-2-ylphenyl)-4-dimethylphosphorylbenzamide Chemical compound C1=CC(P(C)(=O)C)=CC=C1C(=O)NC1=CC(C=2SC=CC=2)=CC=C1N UWHGTSUWTQKZAD-UHFFFAOYSA-N 0.000 claims 1
- HOVUPXXSKYJLES-UHFFFAOYSA-N n-(2-amino-5-thiophen-2-ylphenyl)-6-(diethoxyphosphorylmethyl)pyridine-3-carboxamide Chemical compound C1=NC(CP(=O)(OCC)OCC)=CC=C1C(=O)NC1=CC(C=2SC=CC=2)=CC=C1N HOVUPXXSKYJLES-UHFFFAOYSA-N 0.000 claims 1
- TWSXOUGLLOEMDF-UHFFFAOYSA-N n-(2-amino-5-thiophen-3-ylphenyl)-4-(1-dimethoxyphosphoryl-1-fluoroethyl)benzamide Chemical compound C1=CC(C(C)(F)P(=O)(OC)OC)=CC=C1C(=O)NC1=CC(C2=CSC=C2)=CC=C1N TWSXOUGLLOEMDF-UHFFFAOYSA-N 0.000 claims 1
- FUNWYRCTDYIFGL-UHFFFAOYSA-N n-(2-amino-5-thiophen-3-ylphenyl)-4-(diethoxyphosphorylmethyl)benzamide Chemical compound C1=CC(CP(=O)(OCC)OCC)=CC=C1C(=O)NC1=CC(C2=CSC=C2)=CC=C1N FUNWYRCTDYIFGL-UHFFFAOYSA-N 0.000 claims 1
- REPJIDLFWHRIAQ-UHFFFAOYSA-N n-(2-amino-5-thiophen-3-ylphenyl)-4-[1-fluoro-1-[methoxy(phenyl)phosphoryl]ethyl]benzamide Chemical compound C=1C=C(C(=O)NC=2C(=CC=C(C=2)C2=CSC=C2)N)C=CC=1C(C)(F)P(=O)(OC)C1=CC=CC=C1 REPJIDLFWHRIAQ-UHFFFAOYSA-N 0.000 claims 1
- DLYCRTDCNCHLEX-UHFFFAOYSA-N n-(2-amino-5-thiophen-3-ylphenyl)-4-[[ethoxy(phenyl)phosphoryl]-hydroxymethyl]benzamide Chemical compound C=1C=CC=CC=1P(=O)(OCC)C(O)C(C=C1)=CC=C1C(=O)NC(C(=CC=1)N)=CC=1C=1C=CSC=1 DLYCRTDCNCHLEX-UHFFFAOYSA-N 0.000 claims 1
- UGIJYIJXSCGFDW-UHFFFAOYSA-N n-(2-amino-5-thiophen-3-ylphenyl)-4-[[methoxy(phenyl)phosphoryl]methyl]benzamide Chemical compound C=1C=CC=CC=1P(=O)(OC)CC(C=C1)=CC=C1C(=O)NC(C(=CC=1)N)=CC=1C=1C=CSC=1 UGIJYIJXSCGFDW-UHFFFAOYSA-N 0.000 claims 1
- BEDGPZBFSRIFQC-UHFFFAOYSA-N n-(2-amino-5-thiophen-3-ylphenyl)-4-[dimethoxyphosphoryl(hydroxy)methyl]benzamide Chemical compound C1=CC(C(O)P(=O)(OC)OC)=CC=C1C(=O)NC1=CC(C2=CSC=C2)=CC=C1N BEDGPZBFSRIFQC-UHFFFAOYSA-N 0.000 claims 1
- LQDYJCITOYUCSJ-UHFFFAOYSA-N n-(4-amino-1-phenylpyrazol-3-yl)-4-(diethoxyphosphorylmethyl)benzamide Chemical compound C1=CC(CP(=O)(OCC)OCC)=CC=C1C(=O)NC1=NN(C=2C=CC=CC=2)C=C1N LQDYJCITOYUCSJ-UHFFFAOYSA-N 0.000 claims 1
- PCHFMXSBAFVHEI-UHFFFAOYSA-N n-(4-amino-1-phenylpyrazol-3-yl)-4-[[methoxy(phenyl)phosphoryl]methyl]benzamide Chemical compound C=1C=CC=CC=1P(=O)(OC)CC(C=C1)=CC=C1C(=O)NC(C(=C1)N)=NN1C1=CC=CC=C1 PCHFMXSBAFVHEI-UHFFFAOYSA-N 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims 1
- XHWFEOBQYDSLRB-UHFFFAOYSA-N tert-butyl n-[2-[[4-[3-[ethoxy(methyl)phosphoryl]propanoyl]benzoyl]amino]-4-thiophen-2-ylphenyl]carbamate Chemical compound C1=CC(C(=O)CCP(C)(=O)OCC)=CC=C1C(=O)NC1=CC(C=2SC=CC=2)=CC=C1NC(=O)OC(C)(C)C XHWFEOBQYDSLRB-UHFFFAOYSA-N 0.000 claims 1
- 125000000335 thiazolyl group Chemical group 0.000 claims 1
- 0 CC(C)c1c(C)[s]c(*)c1* Chemical compound CC(C)c1c(C)[s]c(*)c1* 0.000 description 1
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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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| WO2005070020A2 (en) | 2004-01-23 | 2005-08-04 | The Regents Of The University Of Colorado | Gefitinib sensitivity-related gene expression and products and methods related thereto |
| ES2537631T3 (es) | 2004-05-27 | 2015-06-10 | The Regents Of The University Of Colorado | Métodos para la predicción del resultado clínico para inhibidores del receptor del factor de crecimiento epidérmico para pacientes de cáncer |
| JP2009528354A (ja) | 2006-02-28 | 2009-08-06 | メルク エンド カムパニー インコーポレーテッド | ヒストン脱アセチル化酵素のインヒビター |
| EP3103791B1 (en) | 2007-06-27 | 2018-01-31 | Merck Sharp & Dohme Corp. | 4-carboxybenzylamino derivatives as histone deacetylase inhibitors |
| 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 |
| US8420640B2 (en) | 2008-08-29 | 2013-04-16 | Treventis Corporation | Methods of treating amyloid disease using analogs of 1-(4-nitrophenyl) piperazine |
| WO2010028192A1 (en) | 2008-09-03 | 2010-03-11 | Repligen Corporation | Compositions including 6-aminohexanoic acid derivatives as hdac inhibitors |
| WO2012027289A1 (en) * | 2010-08-23 | 2012-03-01 | Syntrix Biosystems Inc. | Aminopyridine- and aminopyrimidinecarboxamides as cxcr2 modulators |
| US9540395B2 (en) | 2011-02-28 | 2017-01-10 | Biomarin Pharmaceutical Inc. | Histone deacetylase inhibitors |
| US8957066B2 (en) | 2011-02-28 | 2015-02-17 | Biomarin Pharmaceutical Inc. | Histone deacetylase inhibitors |
| US10059723B2 (en) | 2011-02-28 | 2018-08-28 | Biomarin Pharmaceutical Inc. | Histone deacetylase inhibitors |
| TWI577693B (zh) | 2011-05-31 | 2017-04-11 | 江蘇康緣藥業股份有限公司 | 聚（ａｄｐ-核糖）聚合酶之三環抑制劑 |
| WO2014018913A2 (en) * | 2012-07-27 | 2014-01-30 | University Of Connecticut | Santacruzamate a compositions and analogs and methods of use |
| CN103665043B (zh) | 2012-08-30 | 2017-11-10 | 江苏豪森药业集团有限公司 | 一种替诺福韦前药及其在医药上的应用 |
| HK1220916A1 (zh) | 2013-03-14 | 2017-05-19 | 基因泰克公司 | 治疗癌症和预防癌症药物抗性的方法 |
| RU2665554C2 (ru) | 2013-03-15 | 2018-08-31 | Байомарин Фармасьютикал Инк. | Ингибиторы hdac |
| WO2015153516A1 (en) * | 2014-04-04 | 2015-10-08 | University Of Florida Research Foundation | Hdac inhibitor compounds and methods of treatment |
| CZ2014915A3 (cs) * | 2014-12-16 | 2016-02-24 | Univerzita Karlova v Praze, Farmaceutická fakulta v Hradci Králové | Substituovaný derivát kyslíkatých kyselin fosforu, jeho použití a farmaceutický přípravek ho obsahující |
| CN104860991B (zh) * | 2015-03-24 | 2017-10-20 | 华南理工大学 | 离子型阴极缓冲层分子型材料及其制备方法和应用 |
| RS62639B1 (sr) | 2015-07-06 | 2021-12-31 | Alkermes Inc | Hetero-halo inhibitori histonskih deacetilaza |
| US10421756B2 (en) | 2015-07-06 | 2019-09-24 | Rodin Therapeutics, Inc. | Heterobicyclic N-aminophenyl-amides as inhibitors of histone deacetylase |
| WO2017127417A1 (en) * | 2016-01-19 | 2017-07-27 | Prospero Pharmaceuticals Llc | Phosphopantothenate compounds |
| CN105859774B (zh) * | 2016-04-12 | 2018-01-19 | 盘锦格林凯默科技有限公司 | 一种膦苯类化合物的制备方法 |
| FR3050732B1 (fr) * | 2016-05-02 | 2019-06-28 | Institut National De La Sante Et De La Recherche Medicale (Inserm) | Nouveaux derives de phosphinolactones et leurs utilisations pharmaceutiques |
| MD3570834T2 (ro) | 2017-01-11 | 2022-04-30 | Alkermes Inc | Inhibitori biciclici ai histon deacetilazei |
| JP7152471B2 (ja) | 2017-08-07 | 2022-10-12 | ロダン・セラピューティクス，インコーポレーテッド | ヒストン脱アセチル化酵素の二環阻害剤 |
| CN112538091B (zh) * | 2020-11-26 | 2022-09-09 | 湖北大学 | 一种双-（对-羧基苯氨基）苯基氧化膦阻燃剂的合成法 |
| CN114685559B (zh) * | 2022-05-16 | 2023-07-18 | 多氟多新材料股份有限公司 | 一种双三氟甲基磷酸锂的制备方法 |
| EP4561586A1 (en) * | 2022-07-28 | 2025-06-04 | The Board of Regents of the University of Oklahoma | Agonists of peroxisome proliferator-activated receptor alpha (ppara) and methods of use |
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| DE1265896B (de) * | 1962-06-19 | 1968-04-11 | Ciba Geigy | Verfahren zur Herstellung von Kuepenfarbstoffen |
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| AU606808B2 (en) * | 1988-06-29 | 1991-02-14 | Otsuka Pharmaceutical Factory, Inc. | Arylcarboxamide substituted by alkylphosphonates, process for preparing the same and a pharmaceutical composition containing the same |
| US5700811A (en) * | 1991-10-04 | 1997-12-23 | Sloan-Kettering Institute For Cancer Research | Potent inducers of terminal differentiation and method of use thereof |
| US5369108A (en) * | 1991-10-04 | 1994-11-29 | Sloan-Kettering Institute For Cancer Research | Potent inducers of terminal differentiation and methods of use thereof |
| JP2787407B2 (ja) * | 1992-06-19 | 1998-08-20 | 株式会社大塚製薬工場 | ホスホン酸ジエステル誘導体 |
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| HUP0202707A3 (en) * | 1999-09-08 | 2003-11-28 | Univ Columbia | Novel class of cytodifferentiating agents and histone deacetylase inhibitors, and pharmaceutical compositions containing them and use thereof |
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| US7868204B2 (en) * | 2001-09-14 | 2011-01-11 | Methylgene Inc. | Inhibitors of histone deacetylase |
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| CN1688577A (zh) | 2002-09-18 | 2005-10-26 | 小野药品工业株式会社 | 三氮杂螺[5.5]十一烷衍生物及以它为活性成分的药物 |
| WO2004058234A2 (en) | 2002-12-27 | 2004-07-15 | Schering Aktiengesellschaft | Pharmaceutical combinations of phthalazine vegf inhibitors and benzamide hdac inhibitors |
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-
2007
- 2007-07-16 EP EP07810507A patent/EP2049124A4/en not_active Withdrawn
- 2007-07-16 JP JP2009520791A patent/JP2009544611A/ja not_active Withdrawn
- 2007-07-16 CA CA002657288A patent/CA2657288A1/en not_active Abandoned
- 2007-07-16 US US12/309,459 patent/US7981874B2/en not_active Expired - Fee Related
- 2007-07-16 WO PCT/US2007/016123 patent/WO2008010985A2/en not_active Ceased
- 2007-07-16 AU AU2007275743A patent/AU2007275743A1/en not_active Abandoned
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