CA2787018A1 - Inhibitors of histone deacetylase (hdac) enzymes - Google Patents
Inhibitors of histone deacetylase (hdac) enzymes Download PDFInfo
- Publication number
- CA2787018A1 CA2787018A1 CA2787018A CA2787018A CA2787018A1 CA 2787018 A1 CA2787018 A1 CA 2787018A1 CA 2787018 A CA2787018 A CA 2787018A CA 2787018 A CA2787018 A CA 2787018A CA 2787018 A1 CA2787018 A1 CA 2787018A1
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- optionally substituted
- methyl
- compound
- 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.)
- Abandoned
Links
- 102000003964 Histone deacetylase Human genes 0.000 title claims description 36
- 108090000353 Histone deacetylase Proteins 0.000 title claims description 36
- 239000003112 inhibitor Substances 0.000 title description 4
- 102000004190 Enzymes Human genes 0.000 title description 2
- 108090000790 Enzymes Proteins 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 393
- 238000000034 method Methods 0.000 claims abstract description 25
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 373
- -1 2,3-dihydro-1,4-benzodioxinyl Chemical group 0.000 claims description 197
- 150000003839 salts Chemical class 0.000 claims description 137
- 125000005843 halogen group Chemical group 0.000 claims description 120
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 117
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 114
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 101
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 83
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 80
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 77
- 125000006526 (C1-C2) alkyl group Chemical group 0.000 claims description 67
- 229910052736 halogen Inorganic materials 0.000 claims description 63
- 150000002367 halogens Chemical class 0.000 claims description 63
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 56
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 53
- 125000003118 aryl group Chemical group 0.000 claims description 50
- 125000004429 atom Chemical group 0.000 claims description 45
- 229910052757 nitrogen Inorganic materials 0.000 claims description 45
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 43
- 125000001424 substituent group Chemical group 0.000 claims description 43
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 42
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 40
- 125000001153 fluoro group Chemical group F* 0.000 claims description 38
- 125000001072 heteroaryl group Chemical group 0.000 claims description 36
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 35
- 125000004076 pyridyl group Chemical group 0.000 claims description 35
- 125000001544 thienyl group Chemical group 0.000 claims description 32
- 125000005842 heteroatom Chemical group 0.000 claims description 29
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 28
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 28
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 25
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 25
- 229910052760 oxygen Inorganic materials 0.000 claims description 23
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 22
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 22
- 229910052717 sulfur Inorganic materials 0.000 claims description 21
- 125000000217 alkyl group Chemical group 0.000 claims description 20
- 239000008194 pharmaceutical composition Substances 0.000 claims description 20
- 125000002971 oxazolyl group Chemical group 0.000 claims description 18
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 17
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 125000004594 isoindolinyl group Chemical group C1(NCC2=CC=CC=C12)* 0.000 claims description 17
- 125000002883 imidazolyl group Chemical group 0.000 claims description 15
- 125000006536 (C1-C2)alkoxy group Chemical group 0.000 claims description 14
- 125000001246 bromo group Chemical group Br* 0.000 claims description 14
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 13
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 12
- 125000001624 naphthyl group Chemical group 0.000 claims description 12
- 125000003386 piperidinyl group Chemical group 0.000 claims description 12
- 125000000335 thiazolyl group Chemical group 0.000 claims description 12
- 125000005871 1,3-benzodioxolyl group Chemical group 0.000 claims description 11
- 125000001425 triazolyl group Chemical group 0.000 claims description 11
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 10
- 125000006528 (C2-C6) alkyl group Chemical group 0.000 claims description 10
- 125000004414 alkyl thio group Chemical group 0.000 claims description 10
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 10
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 9
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 9
- 108010081348 HRT1 protein Hairy Proteins 0.000 claims description 8
- 102100021881 Hairy/enhancer-of-split related with YRPW motif protein 1 Human genes 0.000 claims description 8
- 125000003282 alkyl amino group Chemical group 0.000 claims description 8
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 8
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 7
- 125000005037 alkyl phenyl group Chemical group 0.000 claims description 7
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 7
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 7
- 125000006568 (C4-C7) heterocycloalkyl group Chemical group 0.000 claims description 6
- 125000004193 piperazinyl group Chemical group 0.000 claims description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 6
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 6
- 125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims description 5
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 5
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 5
- 230000002401 inhibitory effect Effects 0.000 claims description 5
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 5
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims description 4
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
- MFGOBRZBIXOVQL-UHFFFAOYSA-N 3-[4-(trifluoromethyl)phenyl]-n-[3-(trifluoromethyl)-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]propanamide Chemical compound O1C(C(F)(F)F)=NC(C=2C(=CC(NC(=O)CCC=3C=CC(=CC=3)C(F)(F)F)=CC=2)C(F)(F)F)=N1 MFGOBRZBIXOVQL-UHFFFAOYSA-N 0.000 claims description 4
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims description 4
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 4
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 4
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 4
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
- 125000001188 haloalkyl group Chemical group 0.000 claims description 4
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 4
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 4
- SWCAWZMNVIXNKH-UHFFFAOYSA-N 3-[1-[3-(3-methyl-1,2-oxazol-5-yl)propyl]indol-5-yl]-5-(trifluoromethyl)-1,2,4-oxadiazole Chemical compound O1N=C(C)C=C1CCCN1C2=CC=C(C=3N=C(ON=3)C(F)(F)F)C=C2C=C1 SWCAWZMNVIXNKH-UHFFFAOYSA-N 0.000 claims description 3
- LIUHKQNWTKDRIU-UHFFFAOYSA-N 3-[7-methyl-1-[4-(3-methyl-1,2-oxazol-5-yl)butyl]indol-5-yl]-5-(trifluoromethyl)-1,2,4-oxadiazole Chemical compound O1N=C(C)C=C1CCCCN1C2=C(C)C=C(C=3N=C(ON=3)C(F)(F)F)C=C2C=C1 LIUHKQNWTKDRIU-UHFFFAOYSA-N 0.000 claims description 3
- 125000002393 azetidinyl group Chemical group 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- PTEDZXDOWHAZEF-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-3-[5-(2,2,2-trifluoroacetyl)thiophen-2-yl]benzamide;n-[(4-fluorophenyl)methyl]-4-[5-(2,2,2-trifluoroacetyl)thiophen-2-yl]benzamide Chemical compound C1=CC(F)=CC=C1CNC(=O)C1=CC=C(C=2SC(=CC=2)C(=O)C(F)(F)F)C=C1.C1=CC(F)=CC=C1CNC(=O)C1=CC=CC(C=2SC(=CC=2)C(=O)C(F)(F)F)=C1 PTEDZXDOWHAZEF-UHFFFAOYSA-N 0.000 claims description 3
- WVXPYMGHPGVJKO-UHFFFAOYSA-N n-benzyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]-1,2,5-oxadiazol-3-amine Chemical compound O1C(C(F)(F)F)=NC(C=2C(=NON=2)NCC=2C=CC=CC=2)=N1 WVXPYMGHPGVJKO-UHFFFAOYSA-N 0.000 claims description 3
- WKKHWEMTBODBGE-UHFFFAOYSA-N 2-(4-methoxyphenyl)-n-[2-[5-(trifluoromethyl)-1h-1,2,4-triazol-3-yl]thiophen-3-yl]acetamide Chemical compound C1=CC(OC)=CC=C1CC(=O)NC1=C(C=2NN=C(N=2)C(F)(F)F)SC=C1 WKKHWEMTBODBGE-UHFFFAOYSA-N 0.000 claims description 2
- NLUHMENALNPHJA-UHFFFAOYSA-N 3-[7-methyl-1-[3-(3-methyl-1,2-oxazol-5-yl)propyl]-2,3-dihydroindol-5-yl]-5-(trifluoromethyl)-1,2,4-oxadiazole Chemical compound O1N=C(C)C=C1CCCN1C2=C(C)C=C(C=3N=C(ON=3)C(F)(F)F)C=C2CC1 NLUHMENALNPHJA-UHFFFAOYSA-N 0.000 claims description 2
- RVFHUKHEFRHUIX-UHFFFAOYSA-N 3-[7-methyl-1-[5-(3-methyl-1,2-oxazol-5-yl)pentyl]indol-5-yl]-5-(trifluoromethyl)-1,2,4-oxadiazole Chemical compound O1N=C(C)C=C1CCCCCN1C2=C(C)C=C(C=3N=C(ON=3)C(F)(F)F)C=C2C=C1 RVFHUKHEFRHUIX-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 2
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 2
- ZYSYLVONVLKOKC-UHFFFAOYSA-N n-[(4-methoxyphenyl)methyl]-4-[5-(trichloromethyl)-1,2,4-oxadiazol-3-yl]-1,2,5-oxadiazol-3-amine Chemical compound C1=CC(OC)=CC=C1CNC1=NON=C1C1=NOC(C(Cl)(Cl)Cl)=N1 ZYSYLVONVLKOKC-UHFFFAOYSA-N 0.000 claims description 2
- 125000003566 oxetanyl group Chemical group 0.000 claims description 2
- PIEXCQIOSMOEOU-UHFFFAOYSA-N 1-bromo-3-chloro-5,5-dimethylimidazolidine-2,4-dione Chemical group CC1(C)N(Br)C(=O)N(Cl)C1=O PIEXCQIOSMOEOU-UHFFFAOYSA-N 0.000 claims 1
- NVCUFLNOWZTXPQ-UHFFFAOYSA-N 3-[7-methyl-2-[4-(3-methyl-1,2-oxazol-5-yl)butyl]-1-benzofuran-5-yl]-5-(trifluoromethyl)-1,2,4-oxadiazole Chemical compound O1N=C(C)C=C1CCCCC1=CC2=CC(C=3N=C(ON=3)C(F)(F)F)=CC(C)=C2O1 NVCUFLNOWZTXPQ-UHFFFAOYSA-N 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 253
- 238000005160 1H NMR spectroscopy Methods 0.000 description 208
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 139
- 239000011541 reaction mixture Substances 0.000 description 139
- 235000019439 ethyl acetate Nutrition 0.000 description 123
- 230000002829 reductive effect Effects 0.000 description 118
- 239000000243 solution Substances 0.000 description 114
- 229910001868 water Inorganic materials 0.000 description 112
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 106
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 105
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 104
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 95
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 87
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 81
- 238000000746 purification Methods 0.000 description 79
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 73
- 238000010992 reflux Methods 0.000 description 71
- 239000007821 HATU Substances 0.000 description 69
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 66
- 239000012044 organic layer Substances 0.000 description 60
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 59
- 239000012267 brine Substances 0.000 description 57
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 57
- 239000007787 solid Substances 0.000 description 57
- ZTOAUVQUTVRHBJ-UHFFFAOYSA-N 3-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzoic acid Chemical compound OC(=O)C1=CC=CC(C=2N=C(ON=2)C(F)(F)F)=C1 ZTOAUVQUTVRHBJ-UHFFFAOYSA-N 0.000 description 51
- 239000000203 mixture Substances 0.000 description 49
- 239000003208 petroleum Substances 0.000 description 45
- 239000012043 crude product Substances 0.000 description 44
- 238000004440 column chromatography Methods 0.000 description 43
- 239000002904 solvent Substances 0.000 description 42
- 239000000047 product Substances 0.000 description 41
- 239000000460 chlorine Chemical group 0.000 description 39
- 239000003480 eluent Substances 0.000 description 38
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 36
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 36
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 36
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
- 239000000741 silica gel Substances 0.000 description 27
- 229910002027 silica gel Inorganic materials 0.000 description 27
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 25
- 229910052938 sodium sulfate Inorganic materials 0.000 description 24
- 235000011152 sodium sulphate Nutrition 0.000 description 24
- OKKJLVBELUTLKV-VMNATFBRSA-N methanol-d1 Chemical compound [2H]OC OKKJLVBELUTLKV-VMNATFBRSA-N 0.000 description 23
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 22
- 239000010410 layer Substances 0.000 description 22
- 239000000377 silicon dioxide Substances 0.000 description 21
- 239000007832 Na2SO4 Substances 0.000 description 20
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 20
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 20
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 19
- 229910000029 sodium carbonate Inorganic materials 0.000 description 19
- 235000017550 sodium carbonate Nutrition 0.000 description 19
- 238000011282 treatment Methods 0.000 description 19
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 18
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 18
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 17
- 201000010099 disease Diseases 0.000 description 17
- ICPJQQSFDRMJCR-UHFFFAOYSA-N 5-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]pyridine-3-carboxylic acid Chemical compound OC(=O)C1=CN=CC(C=2N=C(ON=2)C(F)(F)F)=C1 ICPJQQSFDRMJCR-UHFFFAOYSA-N 0.000 description 16
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 16
- 229910017912 NH2OH Inorganic materials 0.000 description 16
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
- 229960003540 oxyquinoline Drugs 0.000 description 15
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 15
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 14
- 239000007788 liquid Substances 0.000 description 14
- NCCMJENTBCOPQF-UHFFFAOYSA-N [4-(4-phenyl-1,3-thiazol-2-yl)oxan-4-yl]methanamine Chemical compound N=1C(C=2C=CC=CC=2)=CSC=1C1(CN)CCOCC1 NCCMJENTBCOPQF-UHFFFAOYSA-N 0.000 description 13
- 239000002253 acid Substances 0.000 description 12
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 12
- 229910000085 borane Inorganic materials 0.000 description 12
- 239000000284 extract Substances 0.000 description 12
- BHPYMZQTCPRLNR-UHFFFAOYSA-N 2-cyanoethanethioamide Chemical compound NC(=S)CC#N BHPYMZQTCPRLNR-UHFFFAOYSA-N 0.000 description 11
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 11
- 238000005481 NMR spectroscopy Methods 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 11
- 230000000694 effects Effects 0.000 description 11
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 11
- SUNMBRGCANLOEG-UHFFFAOYSA-N 1,3-dichloroacetone Chemical compound ClCC(=O)CCl SUNMBRGCANLOEG-UHFFFAOYSA-N 0.000 description 10
- 102100038720 Histone deacetylase 9 Human genes 0.000 description 10
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 10
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 10
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 10
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 10
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 9
- 206010028980 Neoplasm Diseases 0.000 description 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 9
- 239000001301 oxygen Substances 0.000 description 9
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 9
- 229920006395 saturated elastomer Polymers 0.000 description 9
- 235000017557 sodium bicarbonate Nutrition 0.000 description 9
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
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| BR112014012815A8 (pt) * | 2011-11-28 | 2017-06-20 | Novartis Ag | derivados de trifluormetil-oxadiazol e uso dos mesmos no tratamento de doença |
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| CN104220428A (zh) | 2012-02-03 | 2014-12-17 | 巴斯夫欧洲公司 | 杀真菌嘧啶化合物 |
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| MX2016002199A (es) * | 2013-08-21 | 2016-07-13 | Alios Biopharma Inc | Compuestos antivirales. |
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| JP6483666B2 (ja) | 2013-10-14 | 2019-03-13 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | 選択的に置換されたキノリン化合物 |
| PL226024B1 (pl) * | 2013-10-23 | 2017-06-30 | Wrocławskie Centrum Badań Eit + Spółka Z Ograniczoną | Zastosowanie N-[2-[4-(4-metoksyfenylo)-1,3-tiazol-2-ilo]etylo]- -2-okso-2,5,6,7-tetrahydrocyklopenta[b] pirydyno-3-karboksyamidu |
| UA121116C2 (uk) * | 2014-06-06 | 2020-04-10 | Басф Се | Застосування заміщених оксадіазолів для боротьби з фітопатогенними грибами |
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| JP6660060B2 (ja) | 2014-09-16 | 2020-03-04 | セルジーン クオンティセル リサーチ，インク． | ヒストンデメチラーゼ阻害剤 |
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| WO2016065583A1 (en) | 2014-10-30 | 2016-05-06 | Merck Sharp & Dohme Corp. | Oxazole orexin receptor antagonists |
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| AU2016215432B2 (en) | 2015-02-02 | 2020-07-30 | Valo Early Discovery, Inc. | 3-alkyl-4-amido-bicyclic [4,5,0] hydroxamic acids as HDAC inhibitors |
| AU2016245984B2 (en) | 2015-04-10 | 2021-03-25 | Bioresponse, L.L.C. | Self-emulsifying formulations of DIM-related indoles |
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| JPWO2017014170A1 (ja) | 2015-07-17 | 2018-04-26 | 武田薬品工業株式会社 | 複素環化合物 |
| KR101799005B1 (ko) | 2015-07-27 | 2017-11-17 | 주식회사 종근당 | 히스톤 탈아세틸화효소 6 억제제로서의 1,3,4-옥사다이아졸 설프아마이드 유도체 화합물 및 이를 포함하는 약제학적 조성물 |
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| JP2013517281A (ja) | 2010-01-13 | 2013-05-16 | テンペロ、ファーマシューティカルズ、インコーポレイテッド | 化合物及び方法 |
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- 2011-01-13 BR BR112012017441-0A patent/BR112012017441B1/pt not_active IP Right Cessation
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- 2011-01-13 EA EA201290638A patent/EA022964B1/ru not_active IP Right Cessation
- 2011-01-13 EP EP11733353.4A patent/EP2533783B8/en active Active
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| AU2011205283B2 (en) | 2014-07-10 |
| KR101781663B1 (ko) | 2017-09-25 |
| CN103221047A (zh) | 2013-07-24 |
| MX341133B (es) | 2016-08-08 |
| JP6017313B2 (ja) | 2016-10-26 |
| MX2012008280A (es) | 2012-11-23 |
| BR112012017441B1 (pt) | 2019-11-19 |
| EP2533783B1 (en) | 2015-11-04 |
| EA201290638A1 (ru) | 2013-02-28 |
| CN103221047B (zh) | 2014-12-17 |
| AU2011205283A1 (en) | 2012-08-02 |
| EP2533783A4 (en) | 2013-07-17 |
| IL220939A (en) | 2016-11-30 |
| EA022964B1 (ru) | 2016-03-31 |
| ES2560627T3 (es) | 2016-02-22 |
| JP2013517278A (ja) | 2013-05-16 |
| BR112012017441A2 (pt) | 2016-04-19 |
| ZA201205125B (en) | 2013-03-27 |
| US8901156B2 (en) | 2014-12-02 |
| US20130059883A1 (en) | 2013-03-07 |
| IL220939A0 (en) | 2012-09-24 |
| SG182401A1 (en) | 2012-08-30 |
| EP2533783A1 (en) | 2012-12-19 |
| US20150038534A1 (en) | 2015-02-05 |
| KR20130036093A (ko) | 2013-04-10 |
| EP2533783B8 (en) | 2015-12-16 |
| WO2011088181A1 (en) | 2011-07-21 |
| WO2011088181A9 (en) | 2013-01-31 |
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