JP2013517278A5 - - Google Patents
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- JP2013517278A5 JP2013517278A5 JP2012549064A JP2012549064A JP2013517278A5 JP 2013517278 A5 JP2013517278 A5 JP 2013517278A5 JP 2012549064 A JP2012549064 A JP 2012549064A JP 2012549064 A JP2012549064 A JP 2012549064A JP 2013517278 A5 JP2013517278 A5 JP 2013517278A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- methyl
- optionally substituted
- group
- 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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- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 35
- -1 2,3-dihydro-1,4-benzodioxinyl Chemical group 0.000 claims 28
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 18
- 125000000217 alkyl group Chemical group 0.000 claims 17
- 150000001875 compounds Chemical class 0.000 claims 17
- 150000003839 salts Chemical class 0.000 claims 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 15
- 125000004093 cyano group Chemical group *C#N 0.000 claims 12
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 10
- 229910052736 halogen Inorganic materials 0.000 claims 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims 7
- 150000002367 halogens Chemical class 0.000 claims 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 7
- 125000001544 thienyl group Chemical group 0.000 claims 7
- 125000004429 atom Chemical group 0.000 claims 6
- 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 6
- 125000004076 pyridyl group Chemical group 0.000 claims 6
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 5
- 125000001153 fluoro group Chemical group F* 0.000 claims 5
- 125000004594 isoindolinyl group Chemical group C1(NCC2=CC=CC=C12)* 0.000 claims 5
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 4
- 125000003545 alkoxy group Chemical group 0.000 claims 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 4
- 125000003386 piperidinyl group Chemical group 0.000 claims 4
- 125000001424 substituent group Chemical group 0.000 claims 4
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims 4
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 3
- 125000005871 1,3-benzodioxolyl group Chemical group 0.000 claims 3
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims 3
- 125000001246 bromo group Chemical group Br* 0.000 claims 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 3
- 125000001072 heteroaryl group Chemical group 0.000 claims 3
- 125000005842 heteroatom Chemical group 0.000 claims 3
- 125000002883 imidazolyl group Chemical group 0.000 claims 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 3
- 125000001624 naphthyl group Chemical group 0.000 claims 3
- 125000002971 oxazolyl group Chemical group 0.000 claims 3
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims 2
- 125000004414 alkyl thio group Chemical group 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims 2
- 125000005956 isoquinolyl group Chemical group 0.000 claims 2
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 2
- 125000000335 thiazolyl group Chemical group 0.000 claims 2
- 125000001425 triazolyl group Chemical group 0.000 claims 2
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims 1
- 125000006528 (C2-C6) alkyl group Chemical group 0.000 claims 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- 125000006568 (C4-C7) heterocycloalkyl group Chemical group 0.000 claims 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 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
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- 125000003282 alkyl amino group Chemical group 0.000 claims 1
- 125000002877 alkyl aryl group Chemical group 0.000 claims 1
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims 1
- 125000005037 alkyl phenyl group Chemical group 0.000 claims 1
- 125000002393 azetidinyl group Chemical group 0.000 claims 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims 1
- BRMIYYWPBPHSQY-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-3-[5-(2,2,2-trifluoroacetyl)thiophen-2-yl]benzamide Chemical compound C1=CC(F)=CC=C1CNC(=O)C1=CC=CC(C=2SC(=CC=2)C(=O)C(F)(F)F)=C1 BRMIYYWPBPHSQY-UHFFFAOYSA-N 0.000 claims 1
- JQYWWORDYVNBGY-UHFFFAOYSA-N 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 JQYWWORDYVNBGY-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 125000003566 oxetanyl group Chemical group 0.000 claims 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000004193 piperazinyl group Chemical group 0.000 claims 1
- 125000003226 pyrazolyl group Chemical group 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 1
- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 claims 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US29457510P | 2010-01-13 | 2010-01-13 | |
| US61/294,575 | 2010-01-13 | ||
| PCT/US2011/021089 WO2011088181A1 (en) | 2010-01-13 | 2011-01-13 | Compounds and methods |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2013517278A JP2013517278A (ja) | 2013-05-16 |
| JP2013517278A5 true JP2013517278A5 (enExample) | 2014-03-06 |
| JP6017313B2 JP6017313B2 (ja) | 2016-10-26 |
Family
ID=44304635
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012549064A Expired - Fee Related JP6017313B2 (ja) | 2010-01-13 | 2011-01-13 | 化合物および方法 |
Country Status (15)
| Country | Link |
|---|---|
| US (2) | US8901156B2 (enExample) |
| EP (1) | EP2533783B8 (enExample) |
| JP (1) | JP6017313B2 (enExample) |
| KR (1) | KR101781663B1 (enExample) |
| CN (1) | CN103221047B (enExample) |
| AU (1) | AU2011205283B2 (enExample) |
| BR (1) | BR112012017441B1 (enExample) |
| CA (1) | CA2787018A1 (enExample) |
| EA (1) | EA022964B1 (enExample) |
| ES (1) | ES2560627T3 (enExample) |
| IL (1) | IL220939A (enExample) |
| MX (1) | MX341133B (enExample) |
| SG (1) | SG182401A1 (enExample) |
| WO (1) | WO2011088181A1 (enExample) |
| ZA (1) | ZA201205125B (enExample) |
Families Citing this family (80)
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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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| WO2013066835A2 (en) * | 2011-10-31 | 2013-05-10 | Glaxosmithkline Llc | Compounds and methods |
| ES2606630T3 (es) | 2011-11-28 | 2017-03-24 | Novartis Ag | Derivados de trifluorometil-oxadiazol novedosos y su uso en el tratamiento de enfermedad |
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| KR20220070465A (ko) | 2019-09-27 | 2022-05-31 | 다케다 야쿠힌 고교 가부시키가이샤 | Hdac6 억제제로서 유용한 2-이소인돌-1,3,4-옥사디아졸 유도체 |
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