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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| 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 |
| WO2005117553A2 (en) | 2004-05-27 | 2005-12-15 | The Regents Of The University Of Colorado | Methods for prediction of clinical outcome to epidermal growth factor receptor inhibitors by cancer patients |
| US8168658B2 (en) | 2006-02-28 | 2012-05-01 | Merck Sharp & Dohme Corp. | Inhibitors of histone deacetylase |
| JP2010531358A (ja) * | 2007-06-27 | 2010-09-24 | メルク・シャープ・エンド・ドーム・コーポレイション | ヒストン脱アセチル化酵素阻害剤としてのピリジル及びピリミジニル誘導体 |
| AU2008269154B2 (en) * | 2007-06-27 | 2014-06-12 | Merck Sharp & Dohme Llc | 4-carboxybenzylamino derivatives as histone deacetylase inhibitors |
| JP2012501344A (ja) | 2008-08-29 | 2012-01-19 | トレヴェンティス コーポレイション | アミロイド症を治療する組成物及び方法 |
| US9265734B2 (en) | 2008-09-03 | 2016-02-23 | Biomarin Pharmaceutical Inc. | Compositions including 6-aminohexanoic acid derivatives as HDAC inhibitors |
| JP6486002B2 (ja) * | 2010-08-23 | 2019-03-20 | シントリックス・バイオシステムズ・インコーポレイテッドＳｙｎｔｒｉｘ Ｂｉｏｓｙｓｔｅｍｓ， Ｉｎｃ． | Ｃｘｃｒ２モジュレーターとしてのアミノピリジンカルボキサミドおよびアミノピリミジンカルボキサミド |
| US8957066B2 (en) | 2011-02-28 | 2015-02-17 | Biomarin Pharmaceutical Inc. | Histone deacetylase inhibitors |
| JP6250403B2 (ja) | 2011-02-28 | 2017-12-20 | バイオマリン ファーマシューティカル インク | ヒストン脱アセチル化酵素阻害剤 |
| US10059723B2 (en) | 2011-02-28 | 2018-08-28 | Biomarin Pharmaceutical Inc. | Histone deacetylase inhibitors |
| WO2012166983A1 (en) * | 2011-05-31 | 2012-12-06 | Newgen Therapeutics, Inc. | Tricyclic inhibitors of poly(adp-ribose)polymerase |
| 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 |
| CA2905070A1 (en) | 2013-03-14 | 2014-09-25 | Genentech, Inc. | Methods of treating cancer and preventing cancer drug resistance |
| CA2903490C (en) | 2013-03-15 | 2021-04-13 | Biomarin Pharmaceutical Inc. | Hdac inhibitors |
| US10807944B2 (en) | 2014-04-04 | 2020-10-20 | University Of Florida Research Foundation, Inc. | HDAC inhibitor compounds and methods of treatment |
| CZ305738B6 (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 |
| US20180194769A1 (en) | 2015-07-06 | 2018-07-12 | Rodin Therapeutics, Inc. | Hetero-halo inhibitors of histone deacetylase |
| 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 |
| SI3570834T1 (sl) | 2017-01-11 | 2022-05-31 | Alkermes, Inc. | Biciklični inhibitorji histonske deacetilaze |
| HUE058799T2 (hu) | 2017-08-07 | 2022-09-28 | Alkermes Inc | Hiszton-deacetiláz biciklusos inhibitorai |
| 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 |
| WO2024025862A1 (en) * | 2022-07-28 | 2024-02-01 | The Board Of Regents Of The University Of Oklahoma | Agonists of peroxisome proliferator-activated receptor alpha (ppara) and methods of use |
Family Cites Families (30)
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| US3339999A (en) * | 1962-06-19 | 1967-09-05 | Ciba Ltd | Process for vat dyeing cellulosic textile materials |
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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 |
| JPH11335375A (ja) | 1998-05-20 | 1999-12-07 | Mitsui Chem Inc | ヒストン脱アセチル化酵素阻害作用を有するベンズアミド誘導体 |
| MXPA02002505A (es) * | 1999-09-08 | 2004-09-10 | Sloan Kettering Inst Cancer | Nueva clase de agentes de citodiferenciacion e inhibidores de histona desacetilasa y metodos de utilizacion de los mismos. |
| EP1224186B1 (en) | 1999-10-27 | 2003-09-24 | Millennium Pharmaceuticals, Inc. | Pyridyl-containing spirocyclic compounds as inhibitors of fibrinogen-dependent platelet aggregation |
| AU783504C (en) | 1999-11-23 | 2006-08-03 | Methylgene Inc. | Inhibitors of histone deacetylase |
| CA2432825A1 (en) | 2000-12-15 | 2002-06-20 | Emory University | Nonpeptide agonists and antagonists of vasopressin receptors |
| EP1619194A3 (en) | 2001-03-19 | 2006-06-07 | Ono Pharmaceutical Co., Ltd. | Triazaspiro¬5.5|undecane derivatives and pharmaceutical composition comprising the same as active ingredient |
| AR034897A1 (es) * | 2001-08-07 | 2004-03-24 | Hoffmann La Roche | Derivados n-monoacilados de o-fenilendiaminas, sus analogos heterociclicos de seis miembros y su uso como agentes farmaceuticos |
| US7595343B2 (en) | 2001-09-14 | 2009-09-29 | Methylgene, Inc. | Inhibitors of histone deacetylase |
| US7868204B2 (en) * | 2001-09-14 | 2011-01-11 | Methylgene Inc. | Inhibitors of histone deacetylase |
| US6897220B2 (en) * | 2001-09-14 | 2005-05-24 | Methylgene, Inc. | Inhibitors of histone deacetylase |
| EP1485364B1 (en) | 2002-03-13 | 2009-03-11 | Janssen Pharmaceutica N.V. | Aminocarbonyl-derivatives as novel inhibitors of histone deacetylase |
| BR0307607A (pt) | 2002-03-13 | 2004-12-21 | Janssen Pharmaceutica Nv | Derivados de carbonilamino como inibidores de histona desacetilase |
| DE60320957D1 (en) | 2002-03-13 | 2008-06-26 | Janssen Pharmaceutica Nv | Sulfonylderivate als histone-deacetylase-inhibitoren |
| TWI319387B (en) | 2002-04-05 | 2010-01-11 | Astrazeneca Ab | Benzamide derivatives |
| GB0209715D0 (en) | 2002-04-27 | 2002-06-05 | Astrazeneca Ab | Chemical compounds |
| AU2003272879A1 (en) | 2002-09-18 | 2004-04-08 | Ono Pharmaceutical Co., Ltd. | Triazaspiro[5.5]undecane derivatives and drugs comprising the same as the active ingredient |
| JP2006514991A (ja) | 2002-12-27 | 2006-05-18 | シエーリング アクチエンゲゼルシャフト | 新規医薬組合せ |
| EA011808B1 (ru) | 2003-01-08 | 2009-06-30 | Новартис Вэксинес Энд Дайэгностикс, Инк. | Антибактериальные агенты |
| WO2005030705A1 (en) | 2003-09-24 | 2005-04-07 | Methylgene, Inc. | Inhibitors of histone deacetylase |
| EP1735319B1 (en) | 2004-03-26 | 2017-05-03 | MethylGene Inc. | Inhibitors of histone deacetylase |
| WO2005120515A2 (en) * | 2004-06-10 | 2005-12-22 | Kalypsys, Inc. | Novel sulfonamides as inhibitors of histone deacetylase for the treatment of disease |
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- 2007-07-16 WO PCT/US2007/016123 patent/WO2008010985A2/en active Application Filing
- 2007-07-16 CA CA002657288A patent/CA2657288A1/en not_active Abandoned
- 2007-07-16 JP JP2009520791A patent/JP2009544611A/ja not_active Withdrawn
- 2007-07-16 AU AU2007275743A patent/AU2007275743A1/en not_active Abandoned
- 2007-07-16 EP EP07810507A patent/EP2049124A4/en not_active Withdrawn
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