JP2012515166A5 - - Google Patents
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- JP2012515166A5 JP2012515166A5 JP2011545499A JP2011545499A JP2012515166A5 JP 2012515166 A5 JP2012515166 A5 JP 2012515166A5 JP 2011545499 A JP2011545499 A JP 2011545499A JP 2011545499 A JP2011545499 A JP 2011545499A JP 2012515166 A5 JP2012515166 A5 JP 2012515166A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- carbazol
- dibromo
- propan
- independently selected
- 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.)
- Granted
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- 125000000217 alkyl group Chemical group 0.000 claims description 159
- 229910052757 nitrogen Inorganic materials 0.000 claims description 79
- 125000006413 ring segment Chemical group 0.000 claims description 75
- 125000001072 heteroaryl group Chemical group 0.000 claims description 56
- 229910052760 oxygen Inorganic materials 0.000 claims description 40
- 229910052717 sulfur Inorganic materials 0.000 claims description 40
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 30
- 229910052739 hydrogen Inorganic materials 0.000 claims description 28
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 26
- 125000001188 haloalkyl group Chemical group 0.000 claims description 26
- 125000000623 heterocyclic group Chemical group 0.000 claims description 26
- 239000001257 hydrogen Substances 0.000 claims description 25
- 125000003118 aryl group Chemical group 0.000 claims description 24
- 125000003545 alkoxy group Chemical group 0.000 claims description 17
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 17
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 16
- -1 -NH 2 Chemical group 0.000 claims description 15
- 150000002431 hydrogen Chemical class 0.000 claims description 14
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 14
- 125000005309 thioalkoxy group Chemical group 0.000 claims description 14
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 13
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 12
- 125000005403 thiohaloalkoxy group Chemical group 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 125000002947 alkylene group Chemical group 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 10
- 125000000304 alkynyl group Chemical group 0.000 claims description 8
- 229920006395 saturated elastomer Polymers 0.000 claims description 8
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 7
- 125000004043 oxo group Chemical group O=* 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 125000000464 thioxo group Chemical group S=* 0.000 claims description 4
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 2
- 230000004766 neurogenesis Effects 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims 28
- 150000001875 compounds Chemical class 0.000 claims 21
- 229910052799 carbon Inorganic materials 0.000 claims 6
- TYNCPIWPEXSEIF-UHFFFAOYSA-N 1-(3,6-dibromocarbazol-9-yl)-3-phenoxypropan-2-ol Chemical compound C12=CC=C(Br)C=C2C2=CC(Br)=CC=C2N1CC(O)COC1=CC=CC=C1 TYNCPIWPEXSEIF-UHFFFAOYSA-N 0.000 claims 5
- COEGVAMGKKIGAS-UHFFFAOYSA-N 1-(3-bromo-6-methylcarbazol-9-yl)-3-(3-methoxyanilino)propan-2-ol Chemical compound COC1=CC=CC(NCC(O)CN2C3=CC=C(Br)C=C3C3=CC(C)=CC=C32)=C1 COEGVAMGKKIGAS-UHFFFAOYSA-N 0.000 claims 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 5
- XNLTWMQBJFWQOU-UHFFFAOYSA-N n-[3-(3,6-dibromocarbazol-9-yl)-2-fluoropropyl]-3-methoxyaniline Chemical compound COC1=CC=CC(NCC(F)CN2C3=CC=C(Br)C=C3C3=CC(Br)=CC=C32)=C1 XNLTWMQBJFWQOU-UHFFFAOYSA-N 0.000 claims 5
- LEICNUMXFWNCSJ-UHFFFAOYSA-N 1-(3,6-dibromocarbazol-9-yl)-3-(3-methoxyanilino)propan-2-ol Chemical compound COC1=CC=CC(NCC(O)CN2C3=CC=C(Br)C=C3C3=CC(Br)=CC=C32)=C1 LEICNUMXFWNCSJ-UHFFFAOYSA-N 0.000 claims 4
- OEPQMWPLGZMLLB-UHFFFAOYSA-N 1-(benzenesulfonyl)-3-(3,6-dibromocarbazol-9-yl)propan-2-ol Chemical compound C12=CC=C(Br)C=C2C2=CC(Br)=CC=C2N1CC(O)CS(=O)(=O)C1=CC=CC=C1 OEPQMWPLGZMLLB-UHFFFAOYSA-N 0.000 claims 4
- ZLVSDHUOHBMSTM-UHFFFAOYSA-N 4-anilino-1-(3,6-dibromocarbazol-9-yl)butan-2-ol Chemical compound C12=CC=C(Br)C=C2C2=CC(Br)=CC=C2N1CC(O)CCNC1=CC=CC=C1 ZLVSDHUOHBMSTM-UHFFFAOYSA-N 0.000 claims 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- 125000001841 imino group Chemical group [H]N=* 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- GGGKOOBBMDTVNI-UHFFFAOYSA-N 1,3-bis(3,6-dibromocarbazol-9-yl)propan-2-ol Chemical compound C12=CC=C(Br)C=C2C2=CC(Br)=CC=C2N1CC(O)CN1C2=CC=C(Br)C=C2C2=CC(Br)=CC=C21 GGGKOOBBMDTVNI-UHFFFAOYSA-N 0.000 claims 2
- HLFZENMHWMERSD-UHFFFAOYSA-N 1-(3,6-dibromocarbazol-9-yl)-3-(2-iminopyridin-1-yl)propan-2-ol Chemical compound C12=CC=C(Br)C=C2C2=CC(Br)=CC=C2N1CC(O)CN1C=CC=CC1=N HLFZENMHWMERSD-UHFFFAOYSA-N 0.000 claims 2
- ZPDIUTJLYFGAJQ-UHFFFAOYSA-N 1-(3,6-dibromocarbazol-9-yl)-3-(3,4-dimethylanilino)propan-2-ol Chemical compound C1=C(C)C(C)=CC=C1NCC(O)CN1C2=CC=C(Br)C=C2C2=CC(Br)=CC=C21 ZPDIUTJLYFGAJQ-UHFFFAOYSA-N 0.000 claims 2
- XQECFFFFRVHGKB-UHFFFAOYSA-N 1-(3,6-dibromocarbazol-9-yl)-3-(3,5-dimethylpyrazol-1-yl)propan-2-ol Chemical compound N1=C(C)C=C(C)N1CC(O)CN1C2=CC=C(Br)C=C2C2=CC(Br)=CC=C21 XQECFFFFRVHGKB-UHFFFAOYSA-N 0.000 claims 2
- OTNVUUJXMOOKOR-UHFFFAOYSA-N 1-(3,6-dibromocarbazol-9-yl)-3-(3-methoxyanilino)propan-2-one Chemical compound COC1=CC=CC(NCC(=O)CN2C3=CC=C(Br)C=C3C3=CC(Br)=CC=C32)=C1 OTNVUUJXMOOKOR-UHFFFAOYSA-N 0.000 claims 2
- RHEAMHUORDACEJ-UHFFFAOYSA-N 1-(3,6-dibromocarbazol-9-yl)-3-(3-methylanilino)propan-2-ol Chemical compound CC1=CC=CC(NCC(O)CN2C3=CC=C(Br)C=C3C3=CC(Br)=CC=C32)=C1 RHEAMHUORDACEJ-UHFFFAOYSA-N 0.000 claims 2
- HBKIJADBNAGLQJ-UHFFFAOYSA-N 1-(3,6-dibromocarbazol-9-yl)-3-(pyridin-2-ylamino)propan-2-ol Chemical compound C12=CC=C(Br)C=C2C2=CC(Br)=CC=C2N1CC(O)CNC1=CC=CC=N1 HBKIJADBNAGLQJ-UHFFFAOYSA-N 0.000 claims 2
- XYHMVJPHLBOPSQ-UHFFFAOYSA-N 1-(3,6-dibromocarbazol-9-yl)-3-(pyridin-3-ylamino)propan-2-ol Chemical compound C12=CC=C(Br)C=C2C2=CC(Br)=CC=C2N1CC(O)CNC1=CC=CN=C1 XYHMVJPHLBOPSQ-UHFFFAOYSA-N 0.000 claims 2
- AEHPBIJUYDUOFE-UHFFFAOYSA-N 1-(3,6-dibromocarbazol-9-yl)-3-(pyridin-4-ylamino)propan-2-ol Chemical compound C12=CC=C(Br)C=C2C2=CC(Br)=CC=C2N1CC(O)CNC1=CC=NC=C1 AEHPBIJUYDUOFE-UHFFFAOYSA-N 0.000 claims 2
- XMROYJFDYHWVTC-UHFFFAOYSA-N 1-(3,6-dibromocarbazol-9-yl)-3-(pyrimidin-2-ylamino)propan-2-ol Chemical compound C12=CC=C(Br)C=C2C2=CC(Br)=CC=C2N1CC(O)CNC1=NC=CC=N1 XMROYJFDYHWVTC-UHFFFAOYSA-N 0.000 claims 2
- IEAGWVASODRQOE-UHFFFAOYSA-N 1-(3,6-dibromocarbazol-9-yl)-3-[4-(3-hydroxypropyl)triazol-1-yl]propan-2-ol Chemical compound N1=NC(CCCO)=CN1CC(O)CN1C2=CC=C(Br)C=C2C2=CC(Br)=CC=C21 IEAGWVASODRQOE-UHFFFAOYSA-N 0.000 claims 2
- AUQOJCZVUALAPA-UHFFFAOYSA-N 1-(3,6-dibromocarbazol-9-yl)-3-indol-1-ylpropan-2-ol Chemical compound C12=CC=C(Br)C=C2C2=CC(Br)=CC=C2N1CC(O)CN1C2=CC=CC=C2C=C1 AUQOJCZVUALAPA-UHFFFAOYSA-N 0.000 claims 2
- YZDSOHADUPCFTP-UHFFFAOYSA-N 1-(3,6-dibromocarbazol-9-yl)-3-methoxypropan-2-ol Chemical compound BrC1=CC=C2N(CC(O)COC)C3=CC=C(Br)C=C3C2=C1 YZDSOHADUPCFTP-UHFFFAOYSA-N 0.000 claims 2
- SCVVUROKDVLKEL-UHFFFAOYSA-N 1-(3-aminopyridin-1-ium-1-yl)-3-(3,6-dibromocarbazol-9-yl)propan-2-ol Chemical compound NC1=CC=C[N+](CC(O)CN2C3=CC=C(Br)C=C3C3=CC(Br)=CC=C32)=C1 SCVVUROKDVLKEL-UHFFFAOYSA-N 0.000 claims 2
- BGMJNIZYAWKOOQ-UHFFFAOYSA-N 1-(benzenesulfinyl)-3-(3,6-dibromocarbazol-9-yl)propan-2-ol Chemical compound C12=CC=C(Br)C=C2C2=CC(Br)=CC=C2N1CC(O)CS(=O)C1=CC=CC=C1 BGMJNIZYAWKOOQ-UHFFFAOYSA-N 0.000 claims 2
- XQJGVTRWLPWUEB-UHFFFAOYSA-N 1-carbazol-9-yl-3-(3,6-dibromocarbazol-9-yl)propan-2-ol Chemical compound C12=CC=C(Br)C=C2C2=CC(Br)=CC=C2N1CC(O)CN1C2=CC=CC=C2C2=CC=CC=C21 XQJGVTRWLPWUEB-UHFFFAOYSA-N 0.000 claims 2
- XTXYFNIOWZHKKG-UHFFFAOYSA-N 3-(3,6-dibromocarbazol-9-yl)-1-(3-methoxyanilino)-1-methylsulfanylpropan-2-one Chemical compound COC1=CC=CC(NC(SC)C(=O)CN2C3=CC=C(Br)C=C3C3=CC(Br)=CC=C32)=C1 XTXYFNIOWZHKKG-UHFFFAOYSA-N 0.000 claims 2
- XDUQWKDACCHMSM-UHFFFAOYSA-N 5-[(3,6-dibromocarbazol-9-yl)methyl]-3-(3-methoxyphenyl)-1,3-oxazolidin-2-one Chemical compound COC1=CC=CC(N2C(OC(CN3C4=CC=C(Br)C=C4C4=CC(Br)=CC=C43)C2)=O)=C1 XDUQWKDACCHMSM-UHFFFAOYSA-N 0.000 claims 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 2
- 208000024827 Alzheimer disease Diseases 0.000 claims 2
- 102000014461 Ataxins Human genes 0.000 claims 2
- 108010078286 Ataxins Proteins 0.000 claims 2
- 208000020925 Bipolar disease Diseases 0.000 claims 2
- 206010008025 Cerebellar ataxia Diseases 0.000 claims 2
- 201000010374 Down Syndrome Diseases 0.000 claims 2
- 208000018737 Parkinson disease Diseases 0.000 claims 2
- 208000009415 Spinocerebellar Ataxias Diseases 0.000 claims 2
- 208000030886 Traumatic Brain injury Diseases 0.000 claims 2
- 206010044688 Trisomy 21 Diseases 0.000 claims 2
- 230000032683 aging Effects 0.000 claims 2
- 201000004562 autosomal dominant cerebellar ataxia Diseases 0.000 claims 2
- 125000001246 bromo group Chemical group Br* 0.000 claims 2
- 230000037326 chronic stress Effects 0.000 claims 2
- 125000004122 cyclic group Chemical group 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- 206010015037 epilepsy Diseases 0.000 claims 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 2
- 208000024714 major depressive disease Diseases 0.000 claims 2
- CQANXQNQVSKMDW-UHFFFAOYSA-N n-[2-[3-(3,6-dibromocarbazol-9-yl)-2-hydroxypropoxy]ethyl]acetamide Chemical compound BrC1=CC=C2N(CC(O)COCCNC(=O)C)C3=CC=C(Br)C=C3C2=C1 CQANXQNQVSKMDW-UHFFFAOYSA-N 0.000 claims 2
- YDSSOIJBHGCXDF-UHFFFAOYSA-N n-[3-(3,6-dibromocarbazol-9-yl)-2,2-difluoropropyl]-3-methoxyaniline Chemical group COC1=CC=CC(NCC(F)(F)CN2C3=CC=C(Br)C=C3C3=CC(Br)=CC=C32)=C1 YDSSOIJBHGCXDF-UHFFFAOYSA-N 0.000 claims 2
- WYRPVBNTSWHOJH-UHFFFAOYSA-N n-[3-(3,6-dibromocarbazol-9-yl)-2-fluoropropyl]-3-methoxy-n-methylaniline Chemical compound COC1=CC=CC(N(C)CC(F)CN2C3=CC=C(Br)C=C3C3=CC(Br)=CC=C32)=C1 WYRPVBNTSWHOJH-UHFFFAOYSA-N 0.000 claims 2
- YUWOISVEODOYRL-UHFFFAOYSA-N n-[3-(3,6-dibromocarbazol-9-yl)-2-hydroxypropyl]-n-(3-methoxyphenyl)acetamide Chemical compound COC1=CC=CC(N(CC(O)CN2C3=CC=C(Br)C=C3C3=CC(Br)=CC=C32)C(C)=O)=C1 YUWOISVEODOYRL-UHFFFAOYSA-N 0.000 claims 2
- HEULICAEZQDWSU-UHFFFAOYSA-N n-[3-(3,6-dibromocarbazol-9-yl)-2-methoxypropyl]-3-methoxyaniline Chemical compound C12=CC=C(Br)C=C2C2=CC(Br)=CC=C2N1CC(OC)CNC1=CC=CC(OC)=C1 HEULICAEZQDWSU-UHFFFAOYSA-N 0.000 claims 2
- 230000004770 neurodegeneration Effects 0.000 claims 2
- 208000015122 neurodegenerative disease Diseases 0.000 claims 2
- 208000028173 post-traumatic stress disease Diseases 0.000 claims 2
- 238000001959 radiotherapy Methods 0.000 claims 2
- 201000000980 schizophrenia Diseases 0.000 claims 2
- 230000009529 traumatic brain injury Effects 0.000 claims 2
- IODZDMBFIXBRBA-UHFFFAOYSA-N 1-(2-chloroanilino)-3-(3,6-dibromocarbazol-9-yl)propan-2-ol Chemical compound C12=CC=C(Br)C=C2C2=CC(Br)=CC=C2N1CC(O)CNC1=CC=CC=C1Cl IODZDMBFIXBRBA-UHFFFAOYSA-N 0.000 claims 1
- ZASIEFMZSVPAIK-UHFFFAOYSA-N 1-(3,6-dibromocarbazol-9-yl)-3-(2,3-dimethylanilino)propan-2-ol Chemical compound CC1=CC=CC(NCC(O)CN2C3=CC=C(Br)C=C3C3=CC(Br)=CC=C32)=C1C ZASIEFMZSVPAIK-UHFFFAOYSA-N 0.000 claims 1
- ZPAZLWLHKYMVKG-UHFFFAOYSA-N 1-(3,6-dibromocarbazol-9-yl)-3-(2,4-dimethoxyanilino)propan-2-ol Chemical compound COC1=CC(OC)=CC=C1NCC(O)CN1C2=CC=C(Br)C=C2C2=CC(Br)=CC=C21 ZPAZLWLHKYMVKG-UHFFFAOYSA-N 0.000 claims 1
- NEZLCXSUTUUTCH-UHFFFAOYSA-N 1-(3,6-dibromocarbazol-9-yl)-3-(2,5-dimethylanilino)propan-2-ol Chemical compound CC1=CC=C(C)C(NCC(O)CN2C3=CC=C(Br)C=C3C3=CC(Br)=CC=C32)=C1 NEZLCXSUTUUTCH-UHFFFAOYSA-N 0.000 claims 1
- OXGQUYAYFRUDHS-UHFFFAOYSA-N 1-(3,6-dibromocarbazol-9-yl)-3-(2-hydroxyethylamino)propan-2-ol Chemical compound BrC1=CC=C2N(CC(O)CNCCO)C3=CC=C(Br)C=C3C2=C1 OXGQUYAYFRUDHS-UHFFFAOYSA-N 0.000 claims 1
- MXAYNAQCXCOLSG-UHFFFAOYSA-N 1-(3,6-dibromocarbazol-9-yl)-3-(2-methoxyanilino)propan-2-ol Chemical compound COC1=CC=CC=C1NCC(O)CN1C2=CC=C(Br)C=C2C2=CC(Br)=CC=C21 MXAYNAQCXCOLSG-UHFFFAOYSA-N 0.000 claims 1
- JXJHRNXRRXOEIB-UHFFFAOYSA-N 1-(3,6-dibromocarbazol-9-yl)-3-(2-methylanilino)propan-2-ol Chemical compound CC1=CC=CC=C1NCC(O)CN1C2=CC=C(Br)C=C2C2=CC(Br)=CC=C21 JXJHRNXRRXOEIB-UHFFFAOYSA-N 0.000 claims 1
- UTVAPCQDVLRLDF-UHFFFAOYSA-N 1-(3,6-dibromocarbazol-9-yl)-3-(2-phenylethylamino)propan-2-ol Chemical compound C12=CC=C(Br)C=C2C2=CC(Br)=CC=C2N1CC(O)CNCCC1=CC=CC=C1 UTVAPCQDVLRLDF-UHFFFAOYSA-N 0.000 claims 1
- FVOFWZSDBIAJMJ-UHFFFAOYSA-N 1-(3,6-dibromocarbazol-9-yl)-3-(3,5-dimethylanilino)propan-2-ol Chemical compound CC1=CC(C)=CC(NCC(O)CN2C3=CC=C(Br)C=C3C3=CC(Br)=CC=C32)=C1 FVOFWZSDBIAJMJ-UHFFFAOYSA-N 0.000 claims 1
- GVPHPWUTLBUVGR-UHFFFAOYSA-N 1-(3,6-dibromocarbazol-9-yl)-3-(4-ethoxyanilino)propan-2-ol Chemical compound C1=CC(OCC)=CC=C1NCC(O)CN1C2=CC=C(Br)C=C2C2=CC(Br)=CC=C21 GVPHPWUTLBUVGR-UHFFFAOYSA-N 0.000 claims 1
- JSUUSXDEPORDON-UHFFFAOYSA-N 1-(3,6-dibromocarbazol-9-yl)-3-(4-methoxyanilino)propan-2-ol Chemical compound C1=CC(OC)=CC=C1NCC(O)CN1C2=CC=C(Br)C=C2C2=CC(Br)=CC=C21 JSUUSXDEPORDON-UHFFFAOYSA-N 0.000 claims 1
- STCDAYNMFWTFHH-UHFFFAOYSA-N 1-(3,6-dibromocarbazol-9-yl)-3-(4-methylanilino)propan-2-ol Chemical compound C1=CC(C)=CC=C1NCC(O)CN1C2=CC=C(Br)C=C2C2=CC(Br)=CC=C21 STCDAYNMFWTFHH-UHFFFAOYSA-N 0.000 claims 1
- KYJMBRNIEYPAQO-UHFFFAOYSA-N 1-(3,6-dibromocarbazol-9-yl)-3-(naphthalen-1-ylamino)propan-2-ol Chemical compound C12=CC=C(Br)C=C2C2=CC(Br)=CC=C2N1CC(O)CNC1=CC=CC2=CC=CC=C12 KYJMBRNIEYPAQO-UHFFFAOYSA-N 0.000 claims 1
- SSUUCJHSTMIBDY-UHFFFAOYSA-N 1-(3,6-dibromocarbazol-9-yl)-3-(propan-2-ylamino)propan-2-ol Chemical compound BrC1=CC=C2N(CC(O)CNC(C)C)C3=CC=C(Br)C=C3C2=C1 SSUUCJHSTMIBDY-UHFFFAOYSA-N 0.000 claims 1
- UNXYFVAPLFKBDC-UHFFFAOYSA-N 1-(3,6-dibromocarbazol-9-yl)-3-phenylsulfanylpropan-2-ol Chemical compound C12=CC=C(Br)C=C2C2=CC(Br)=CC=C2N1CC(O)CSC1=CC=CC=C1 UNXYFVAPLFKBDC-UHFFFAOYSA-N 0.000 claims 1
- BGLSOFRVASDQKE-UHFFFAOYSA-N 1-(3,6-dichlorocarbazol-9-yl)-3-(3-methoxyanilino)propan-2-ol Chemical compound COC1=CC=CC(NCC(O)CN2C3=CC=C(Cl)C=C3C3=CC(Cl)=CC=C32)=C1 BGLSOFRVASDQKE-UHFFFAOYSA-N 0.000 claims 1
- JIBZEAFLCBSEIL-UHFFFAOYSA-N 1-(3,6-dichlorocarbazol-9-yl)-3-(4-methylanilino)propan-2-ol Chemical compound C1=CC(C)=CC=C1NCC(O)CN1C2=CC=C(Cl)C=C2C2=CC(Cl)=CC=C21 JIBZEAFLCBSEIL-UHFFFAOYSA-N 0.000 claims 1
- UJZUUJOXOZCQNZ-UHFFFAOYSA-N 1-(3-bromocarbazol-9-yl)-3-(3-methoxyanilino)propan-2-ol Chemical compound COC1=CC=CC(NCC(O)CN2C3=CC=C(Br)C=C3C3=CC=CC=C32)=C1 UJZUUJOXOZCQNZ-UHFFFAOYSA-N 0.000 claims 1
- UXKLJRMGMUBVRB-UHFFFAOYSA-N 1-(4-bromoanilino)-3-(3,6-dibromocarbazol-9-yl)propan-2-ol Chemical compound C12=CC=C(Br)C=C2C2=CC(Br)=CC=C2N1CC(O)CNC1=CC=C(Br)C=C1 UXKLJRMGMUBVRB-UHFFFAOYSA-N 0.000 claims 1
- NDSIFUBZUKXXRP-UHFFFAOYSA-N 1-(4-bromoanilino)-3-(3,6-dichlorocarbazol-9-yl)propan-2-ol Chemical compound C12=CC=C(Cl)C=C2C2=CC(Cl)=CC=C2N1CC(O)CNC1=CC=C(Br)C=C1 NDSIFUBZUKXXRP-UHFFFAOYSA-N 0.000 claims 1
- DYCPSFQUXZLXPW-UHFFFAOYSA-N 1-(4-chloroanilino)-3-(3,6-dibromocarbazol-9-yl)propan-2-ol Chemical compound C12=CC=C(Br)C=C2C2=CC(Br)=CC=C2N1CC(O)CNC1=CC=C(Cl)C=C1 DYCPSFQUXZLXPW-UHFFFAOYSA-N 0.000 claims 1
- CDKKRSGGFNLVQB-UHFFFAOYSA-N 1-(benzylamino)-3-carbazol-9-ylpropan-2-ol Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1CC(O)CNCC1=CC=CC=C1 CDKKRSGGFNLVQB-UHFFFAOYSA-N 0.000 claims 1
- VBMYXYXSKXYBKK-UHFFFAOYSA-N 1-(tert-butylamino)-3-(3,6-dibromocarbazol-9-yl)propan-2-ol Chemical compound BrC1=CC=C2N(CC(O)CNC(C)(C)C)C3=CC=C(Br)C=C3C2=C1 VBMYXYXSKXYBKK-UHFFFAOYSA-N 0.000 claims 1
- BAZZBLWVLQDKLN-UHFFFAOYSA-N 1-amino-3-(3,6-dibromocarbazol-9-yl)propan-2-ol Chemical compound BrC1=CC=C2N(CC(O)CN)C3=CC=C(Br)C=C3C2=C1 BAZZBLWVLQDKLN-UHFFFAOYSA-N 0.000 claims 1
- XWAJZQYHOAQIMX-UHFFFAOYSA-N 1-anilino-3-(3,6-dibromopyrido[3,4-b]indol-9-yl)propan-2-ol Chemical compound C12=CC=C(Br)C=C2C2=CC(Br)=NC=C2N1CC(O)CNC1=CC=CC=C1 XWAJZQYHOAQIMX-UHFFFAOYSA-N 0.000 claims 1
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-
2010
- 2010-01-11 WO PCT/US2010/020681 patent/WO2010081115A1/en not_active Ceased
- 2010-01-11 US US12/685,652 patent/US8604074B2/en not_active Expired - Fee Related
- 2010-01-11 CN CN201080007207.1A patent/CN102405043B/zh not_active Expired - Fee Related
- 2010-01-11 EP EP10711784.8A patent/EP2385829B1/en not_active Not-in-force
- 2010-01-11 CA CA2748813A patent/CA2748813C/en not_active Expired - Fee Related
- 2010-01-11 JP JP2011545499A patent/JP5766614B2/ja not_active Expired - Fee Related
- 2010-01-11 AU AU2010203356A patent/AU2010203356B2/en not_active Ceased
- 2010-01-11 CN CN201710811262.XA patent/CN107595841A/zh active Pending
- 2010-01-11 BR BRPI1006825A patent/BRPI1006825A2/pt not_active Application Discontinuation
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2011
- 2011-07-07 IL IL213992A patent/IL213992A/en active IP Right Grant
-
2013
- 2013-12-09 US US14/100,515 patent/US9278923B2/en not_active Expired - Fee Related
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2014
- 2014-07-24 US US14/339,742 patent/US9156787B2/en not_active Expired - Fee Related
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2016
- 2016-01-15 US US14/996,596 patent/US10172827B2/en not_active Expired - Fee Related
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