JP2008501771A5 - - Google Patents
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- JP2008501771A5 JP2008501771A5 JP2007526538A JP2007526538A JP2008501771A5 JP 2008501771 A5 JP2008501771 A5 JP 2008501771A5 JP 2007526538 A JP2007526538 A JP 2007526538A JP 2007526538 A JP2007526538 A JP 2007526538A JP 2008501771 A5 JP2008501771 A5 JP 2008501771A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- amino
- vinyl
- benzamide
- phenyl
- 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 83
- -1 cyano, hydroxy Chemical group 0.000 claims 36
- 229910052757 nitrogen Inorganic materials 0.000 claims 29
- 125000000623 heterocyclic group Chemical group 0.000 claims 18
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 17
- 150000001875 compounds Chemical class 0.000 claims 17
- 125000003118 aryl group Chemical group 0.000 claims 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 12
- 125000001475 halogen functional group Chemical group 0.000 claims 12
- 238000000034 method Methods 0.000 claims 11
- 229910052799 carbon Inorganic materials 0.000 claims 9
- ZYHQGITXIJDDKC-UHFFFAOYSA-N 2-[2-(2-aminophenyl)ethyl]aniline Chemical group NC1=CC=CC=C1CCC1=CC=CC=C1N ZYHQGITXIJDDKC-UHFFFAOYSA-N 0.000 claims 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 8
- 125000003545 alkoxy group Chemical group 0.000 claims 8
- 125000001589 carboacyl group Chemical group 0.000 claims 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 8
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims 7
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 7
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 7
- 125000004423 acyloxy group Chemical group 0.000 claims 7
- 125000005236 alkanoylamino group Chemical group 0.000 claims 7
- 150000001408 amides Chemical class 0.000 claims 7
- 150000002148 esters Chemical class 0.000 claims 7
- 238000001727 in vivo Methods 0.000 claims 7
- 150000003839 salts Chemical class 0.000 claims 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 5
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 5
- 239000003814 drug Substances 0.000 claims 5
- 229910052739 hydrogen Inorganic materials 0.000 claims 5
- 239000001257 hydrogen Substances 0.000 claims 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 5
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 4
- 150000001361 allenes Chemical class 0.000 claims 4
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 4
- 239000003054 catalyst Substances 0.000 claims 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 4
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims 4
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 3
- 206010028980 Neoplasm Diseases 0.000 claims 3
- 201000011510 cancer Diseases 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- PYYDVQPOSYCSSO-UHFFFAOYSA-N n-(2-aminophenyl)-4-[3-(3,4-dihydro-1h-isoquinolin-2-yl)prop-1-en-2-yl]benzamide Chemical compound NC1=CC=CC=C1NC(=O)C1=CC=C(C(=C)CN2CC3=CC=CC=C3CC2)C=C1 PYYDVQPOSYCSSO-UHFFFAOYSA-N 0.000 claims 3
- 239000012038 nucleophile Substances 0.000 claims 3
- 239000011347 resin Substances 0.000 claims 3
- 229920005989 resin Polymers 0.000 claims 3
- 229920002554 vinyl polymer Polymers 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical group [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 2
- 125000003342 alkenyl group Chemical group 0.000 claims 2
- 125000000304 alkynyl group Chemical group 0.000 claims 2
- 125000004104 aryloxy group Chemical group 0.000 claims 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 2
- 230000024245 cell differentiation Effects 0.000 claims 2
- 230000004663 cell proliferation Effects 0.000 claims 2
- 239000003153 chemical reaction reagent Substances 0.000 claims 2
- 230000008878 coupling Effects 0.000 claims 2
- 238000010168 coupling process Methods 0.000 claims 2
- 238000005859 coupling reaction Methods 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 208000035475 disorder Diseases 0.000 claims 2
- 239000007789 gas Substances 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- YSQCHDWGPQOLNP-UHFFFAOYSA-N n-(2-aminophenyl)-4-[3-(1,3,4,9-tetrahydropyrido[3,4-b]indol-2-yl)prop-1-en-2-yl]benzamide Chemical compound NC1=CC=CC=C1NC(=O)C1=CC=C(C(=C)CN2CC3=C(C4=CC=CC=C4N3)CC2)C=C1 YSQCHDWGPQOLNP-UHFFFAOYSA-N 0.000 claims 2
- KRYHMGNCIHZKPA-UHFFFAOYSA-N n-(2-aminophenyl)-4-[3-[4-(2-fluorophenyl)piperazin-1-yl]prop-1-en-2-yl]benzamide Chemical compound NC1=CC=CC=C1NC(=O)C1=CC=C(C(=C)CN2CCN(CC2)C=2C(=CC=CC=2)F)C=C1 KRYHMGNCIHZKPA-UHFFFAOYSA-N 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 239000001301 oxygen Substances 0.000 claims 2
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical group NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 claims 1
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- UZZMRZLBHCPIMP-UHFFFAOYSA-M 4-(4,6-dimethoxy-2h-1,3,5-triazin-1-yl)-4-methylmorpholin-4-ium;chloride Chemical group [Cl-].COC1=NC(OC)=NCN1[N+]1(C)CCOCC1 UZZMRZLBHCPIMP-UHFFFAOYSA-M 0.000 claims 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
- JDDWRLPTKIOUOF-UHFFFAOYSA-N 9h-fluoren-9-ylmethyl n-[[4-[2-[bis(4-methylphenyl)methylamino]-2-oxoethoxy]phenyl]-(2,4-dimethoxyphenyl)methyl]carbamate Chemical compound COC1=CC(OC)=CC=C1C(C=1C=CC(OCC(=O)NC(C=2C=CC(C)=CC=2)C=2C=CC(C)=CC=2)=CC=1)NC(=O)OCC1C2=CC=CC=C2C2=CC=CC=C21 JDDWRLPTKIOUOF-UHFFFAOYSA-N 0.000 claims 1
- 206010006187 Breast cancer Diseases 0.000 claims 1
- 208000026310 Breast neoplasm Diseases 0.000 claims 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- 201000009030 Carcinoma Diseases 0.000 claims 1
- 206010009944 Colon cancer Diseases 0.000 claims 1
- 208000008839 Kidney Neoplasms Diseases 0.000 claims 1
- 206010033128 Ovarian cancer Diseases 0.000 claims 1
- 206010061535 Ovarian neoplasm Diseases 0.000 claims 1
- 206010038389 Renal cancer Diseases 0.000 claims 1
- 206010039491 Sarcoma Diseases 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 1
- 125000003368 amide group Chemical group 0.000 claims 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 125000002837 carbocyclic group Chemical group 0.000 claims 1
- 150000001721 carbon Chemical group 0.000 claims 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims 1
- 208000029742 colonic neoplasm Diseases 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- 230000003394 haemopoietic effect Effects 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
- 125000001041 indolyl group Chemical group 0.000 claims 1
- 229910052740 iodine Inorganic materials 0.000 claims 1
- 239000011630 iodine Substances 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 201000010982 kidney cancer Diseases 0.000 claims 1
- 208000032839 leukemia Diseases 0.000 claims 1
- 201000001441 melanoma Diseases 0.000 claims 1
- 206010061289 metastatic neoplasm Diseases 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 1
- 125000002757 morpholinyl group Chemical group 0.000 claims 1
- VEJIBCSPTDYTHF-UHFFFAOYSA-N n-(2-aminophenyl)-2-[4-(3-morpholin-4-ylprop-1-en-2-yl)phenyl]acetamide Chemical compound NC1=CC=CC=C1NC(=O)CC1=CC=C(C(=C)CN2CCOCC2)C=C1 VEJIBCSPTDYTHF-UHFFFAOYSA-N 0.000 claims 1
- JYOHGKSWRLTIMH-UHFFFAOYSA-N n-(2-aminophenyl)-4-(3-morpholin-4-ylprop-1-en-2-yl)benzamide Chemical compound NC1=CC=CC=C1NC(=O)C1=CC=C(C(=C)CN2CCOCC2)C=C1 JYOHGKSWRLTIMH-UHFFFAOYSA-N 0.000 claims 1
- YLYWBDCVHLSZST-UHFFFAOYSA-N n-(2-aminophenyl)-4-[1-(3,4-dihydro-1h-isoquinolin-2-yl)-3-methylbut-2-en-2-yl]benzamide Chemical compound C1CC2=CC=CC=C2CN1CC(=C(C)C)C(C=C1)=CC=C1C(=O)NC1=CC=CC=C1N YLYWBDCVHLSZST-UHFFFAOYSA-N 0.000 claims 1
- GATWDTJNFBMKRK-UHFFFAOYSA-N n-(2-aminophenyl)-4-[3-(2-chlorophenothiazin-10-yl)prop-1-en-2-yl]benzamide Chemical compound NC1=CC=CC=C1NC(=O)C1=CC=C(C(=C)CN2C3=CC(Cl)=CC=C3SC3=CC=CC=C32)C=C1 GATWDTJNFBMKRK-UHFFFAOYSA-N 0.000 claims 1
- XHKXHRHDEKHOBA-UHFFFAOYSA-N n-(2-aminophenyl)-4-[3-(4-pyridin-2-ylpiperazin-1-yl)prop-1-en-2-yl]benzamide Chemical compound NC1=CC=CC=C1NC(=O)C1=CC=C(C(=C)CN2CCN(CC2)C=2N=CC=CC=2)C=C1 XHKXHRHDEKHOBA-UHFFFAOYSA-N 0.000 claims 1
- VGHQGXLWUQBSQS-UHFFFAOYSA-N n-(2-aminophenyl)-4-[3-(9-oxoacridin-10-yl)prop-1-en-2-yl]benzamide Chemical compound NC1=CC=CC=C1NC(=O)C1=CC=C(C(=C)CN2C3=CC=CC=C3C(=O)C3=CC=CC=C32)C=C1 VGHQGXLWUQBSQS-UHFFFAOYSA-N 0.000 claims 1
- YTUXOVDFKUAGIW-UHFFFAOYSA-N n-(2-aminophenyl)-4-[3-(benzylamino)prop-1-en-2-yl]benzamide Chemical compound NC1=CC=CC=C1NC(=O)C1=CC=C(C(=C)CNCC=2C=CC=CC=2)C=C1 YTUXOVDFKUAGIW-UHFFFAOYSA-N 0.000 claims 1
- UHPZIWSYZIIXPP-UHFFFAOYSA-N n-(2-aminophenyl)-4-[3-(pyridin-3-ylmethylamino)prop-1-en-2-yl]benzamide Chemical compound NC1=CC=CC=C1NC(=O)C1=CC=C(C(=C)CNCC=2C=NC=CC=2)C=C1 UHPZIWSYZIIXPP-UHFFFAOYSA-N 0.000 claims 1
- AEBYMKMBNUABEF-UHFFFAOYSA-N n-(2-aminophenyl)-4-[3-[4-(2-methoxyphenyl)piperazin-1-yl]prop-1-en-2-yl]benzamide Chemical compound COC1=CC=CC=C1N1CCN(CC(=C)C=2C=CC(=CC=2)C(=O)NC=2C(=CC=CC=2)N)CC1 AEBYMKMBNUABEF-UHFFFAOYSA-N 0.000 claims 1
- MSKFDACWWCUNHV-UHFFFAOYSA-N n-(2-aminophenyl)-4-[3-[4-(3-chloro-4-fluorophenyl)piperazin-1-yl]prop-1-en-2-yl]benzamide Chemical compound NC1=CC=CC=C1NC(=O)C1=CC=C(C(=C)CN2CCN(CC2)C=2C=C(Cl)C(F)=CC=2)C=C1 MSKFDACWWCUNHV-UHFFFAOYSA-N 0.000 claims 1
- RHPJERGEAGJTDM-UHFFFAOYSA-N n-(2-aminophenyl)-4-[3-[4-(3-fluorophenyl)piperazin-1-yl]prop-1-en-2-yl]benzamide Chemical compound NC1=CC=CC=C1NC(=O)C1=CC=C(C(=C)CN2CCN(CC2)C=2C=C(F)C=CC=2)C=C1 RHPJERGEAGJTDM-UHFFFAOYSA-N 0.000 claims 1
- ATBQIQJSNGYLAO-UHFFFAOYSA-N n-(2-aminophenyl)-4-[3-[4-(4-chloro-2-fluorophenyl)piperazin-1-yl]prop-1-en-2-yl]benzamide Chemical compound NC1=CC=CC=C1NC(=O)C1=CC=C(C(=C)CN2CCN(CC2)C=2C(=CC(Cl)=CC=2)F)C=C1 ATBQIQJSNGYLAO-UHFFFAOYSA-N 0.000 claims 1
- AYIVFHHHEMCKRD-UHFFFAOYSA-N n-(2-aminophenyl)-4-[3-[4-(4-fluorophenyl)piperazin-1-yl]prop-1-en-2-yl]benzamide Chemical compound NC1=CC=CC=C1NC(=O)C1=CC=C(C(=C)CN2CCN(CC2)C=2C=CC(F)=CC=2)C=C1 AYIVFHHHEMCKRD-UHFFFAOYSA-N 0.000 claims 1
- VVRQPEBOABQSGA-UHFFFAOYSA-N n-(2-aminophenyl)-4-[3-[4-[3,5-bis(trifluoromethyl)phenyl]piperazin-1-yl]prop-1-en-2-yl]benzamide Chemical compound NC1=CC=CC=C1NC(=O)C1=CC=C(C(=C)CN2CCN(CC2)C=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)C=C1 VVRQPEBOABQSGA-UHFFFAOYSA-N 0.000 claims 1
- KGKIJZLKEXXQMR-UHFFFAOYSA-N n-(2-aminophenyl)-4-[3-[benzyl(methyl)amino]prop-1-en-2-yl]benzamide Chemical compound C=1C=CC=CC=1CN(C)CC(=C)C(C=C1)=CC=C1C(=O)NC1=CC=CC=C1N KGKIJZLKEXXQMR-UHFFFAOYSA-N 0.000 claims 1
- GUDLICWMFXQJFP-UHFFFAOYSA-N n-(2-aminophenyl)-4-[4-(3-morpholin-4-ylprop-1-en-2-yl)phenyl]butanamide Chemical compound NC1=CC=CC=C1NC(=O)CCCC1=CC=C(C(=C)CN2CCOCC2)C=C1 GUDLICWMFXQJFP-UHFFFAOYSA-N 0.000 claims 1
- RFDVMOUXHKTCDO-UHFFFAOYSA-N n-(2-aminophenyl)benzamide Chemical compound NC1=CC=CC=C1NC(=O)C1=CC=CC=C1 RFDVMOUXHKTCDO-UHFFFAOYSA-N 0.000 claims 1
- MXFRKMUZBXJMKB-UHFFFAOYSA-N n-(2-aminopyridin-3-yl)-4-[3-(pyridin-3-ylmethylamino)prop-1-en-2-yl]benzamide Chemical compound NC1=NC=CC=C1NC(=O)C1=CC=C(C(=C)CNCC=2C=NC=CC=2)C=C1 MXFRKMUZBXJMKB-UHFFFAOYSA-N 0.000 claims 1
- 230000001613 neoplastic effect Effects 0.000 claims 1
- 208000002154 non-small cell lung carcinoma Diseases 0.000 claims 1
- 230000000269 nucleophilic effect Effects 0.000 claims 1
- 125000002971 oxazolyl group Chemical group 0.000 claims 1
- 229910052763 palladium Inorganic materials 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims 1
- 125000004193 piperazinyl group Chemical group 0.000 claims 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 125000004574 piperidin-2-yl group Chemical group N1C(CCCC1)* 0.000 claims 1
- 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 claims 1
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- 229920000642 polymer Polymers 0.000 claims 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims 1
- 125000003373 pyrazinyl group Chemical group 0.000 claims 1
- 125000003226 pyrazolyl group Chemical group 0.000 claims 1
- 125000002098 pyridazinyl group Chemical group 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
- 125000005493 quinolyl group Chemical group 0.000 claims 1
- 239000007790 solid phase Substances 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 239000011593 sulfur Substances 0.000 claims 1
- 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 claims 1
- 125000000335 thiazolyl group Chemical group 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- 125000004306 triazinyl group Chemical group 0.000 claims 1
- 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 claims 1
- 0 C=C(C*C(c1ccccc1)=O)c(cc1)ccc1C(Nc1ccccc1N)=O Chemical compound C=C(C*C(c1ccccc1)=O)c(cc1)ccc1C(Nc1ccccc1N)=O 0.000 description 3
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US57891504P | 2004-06-10 | 2004-06-10 | |
| GB0412964A GB0412964D0 (en) | 2004-06-10 | 2004-06-10 | Inhibitors of histone deacetylase |
| PCT/GB2005/002234 WO2005121073A1 (en) | 2004-06-10 | 2005-06-07 | Inhibitors of histone deacetylase |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2008501771A JP2008501771A (ja) | 2008-01-24 |
| JP2008501771A5 true JP2008501771A5 (enExample) | 2008-07-17 |
Family
ID=34970964
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007526538A Withdrawn JP2008501771A (ja) | 2004-06-10 | 2005-06-07 | ヒストン脱アセチル化酵素阻害剤 |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US20080234254A1 (enExample) |
| EP (1) | EP1758847A1 (enExample) |
| JP (1) | JP2008501771A (enExample) |
| WO (1) | WO2005121073A1 (enExample) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2642813A1 (en) | 2006-02-28 | 2007-09-07 | Merck & Co., Inc. | Inhibitors of histone deacetylase |
| KR20100074288A (ko) * | 2007-10-22 | 2010-07-01 | 오키드 리서치 레버라토리즈 리미티드 | 히스톤 디아세틸라제 억제제 |
| AU2009289649B2 (en) | 2008-09-03 | 2016-05-05 | Biomarin Pharmaceutical Inc. | Compositions including 6-aminohexanoic acid derivatives as HDAC inhibitors |
| CN102249958B (zh) * | 2010-11-29 | 2014-06-04 | 江苏先声药物研究有限公司 | 苯甲酰氨类组蛋白去乙酰化酶抑制剂 |
| 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 |
| 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 |
| CN102807526B (zh) * | 2011-06-21 | 2015-12-02 | 寿光富康制药有限公司 | 组蛋白去乙酰化酶抑制剂ZYJ-D08a及其差向异构体的制备方法与应用 |
| GB201111630D0 (en) | 2011-07-07 | 2011-08-24 | Cancer Rec Tech Ltd | Novel compounds and their use |
| WO2013169858A1 (en) | 2012-05-08 | 2013-11-14 | The Broad Institute, Inc. | Diagnostic and treatment methods in patients having or at risk of developing resistance to cancer therapy |
| PT2970139T (pt) | 2013-03-15 | 2018-08-01 | Biomarin Pharm Inc | Inibidores de hdac |
| EP3062783B1 (en) | 2013-10-18 | 2020-08-12 | The General Hospital Corporation | Imaging histone deacetylases with a radiotracer using positron emission tomography |
| EP3237390B1 (en) | 2014-12-23 | 2019-05-08 | Crossing S.r.l. | Method for the industrial production of 2-halo-4,6-dialkoxy-1,3,5-triazine and their use in the presence of amines |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6174905B1 (en) * | 1996-09-30 | 2001-01-16 | Mitsui Chemicals, Inc. | Cell differentiation inducer |
| EP1551795A1 (en) * | 2002-10-17 | 2005-07-13 | Methylgene, Inc. | Inhibitors of histone deacetylase |
-
2005
- 2005-06-07 US US11/628,992 patent/US20080234254A1/en not_active Abandoned
- 2005-06-07 JP JP2007526538A patent/JP2008501771A/ja not_active Withdrawn
- 2005-06-07 EP EP05754307A patent/EP1758847A1/en not_active Withdrawn
- 2005-06-07 WO PCT/GB2005/002234 patent/WO2005121073A1/en not_active Ceased
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