JP2008536876A5 - - Google Patents
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- JP2008536876A5 JP2008536876A5 JP2008506824A JP2008506824A JP2008536876A5 JP 2008536876 A5 JP2008536876 A5 JP 2008536876A5 JP 2008506824 A JP2008506824 A JP 2008506824A JP 2008506824 A JP2008506824 A JP 2008506824A JP 2008536876 A5 JP2008536876 A5 JP 2008536876A5
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- JP
- Japan
- Prior art keywords
- group
- pyrido
- indole
- alkyl
- substituted
- 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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- 125000003118 aryl group Chemical group 0.000 claims 22
- -1 acetamino, thio Chemical group 0.000 claims 20
- 125000000623 heterocyclic group Chemical group 0.000 claims 19
- 150000001875 compounds Chemical class 0.000 claims 16
- 206010028980 Neoplasm Diseases 0.000 claims 15
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 15
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 13
- 125000000217 alkyl group Chemical group 0.000 claims 12
- 230000001548 androgenic effect Effects 0.000 claims 11
- 125000001072 heteroaryl group Chemical group 0.000 claims 9
- 125000003282 alkyl amino group Chemical group 0.000 claims 8
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 7
- 125000003277 amino group Chemical group 0.000 claims 7
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 6
- 229910052736 halogen Inorganic materials 0.000 claims 6
- 150000002367 halogens Chemical group 0.000 claims 6
- 229910052739 hydrogen Inorganic materials 0.000 claims 6
- 239000001257 hydrogen Substances 0.000 claims 6
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 5
- 201000011510 cancer Diseases 0.000 claims 5
- 125000004043 oxo group Chemical group O=* 0.000 claims 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 4
- JXDYKVIHCLTXOP-UHFFFAOYSA-N isatin Chemical compound C1=CC=C2C(=O)C(=O)NC2=C1 JXDYKVIHCLTXOP-UHFFFAOYSA-N 0.000 claims 4
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 claims 4
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 4
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 3
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims 3
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims 3
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims 3
- 125000003545 alkoxy group Chemical group 0.000 claims 3
- 125000004414 alkyl thio group Chemical group 0.000 claims 3
- 238000010171 animal model Methods 0.000 claims 3
- 239000003795 chemical substances by application Substances 0.000 claims 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 239000012453 solvate Substances 0.000 claims 3
- MYKCASYWEDUQLZ-UHFFFAOYSA-N 1-(6-methoxy-1-methyl-1,3,4,9-tetrahydropyrido[3,4-b]indol-2-yl)ethanone Chemical compound CC1N(C(C)=O)CCC2=C1NC1=CC=C(OC)C=C12 MYKCASYWEDUQLZ-UHFFFAOYSA-N 0.000 claims 2
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 2
- GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 claims 2
- 229930012538 Paclitaxel Natural products 0.000 claims 2
- 102000005789 Vascular Endothelial Growth Factors Human genes 0.000 claims 2
- 108010019530 Vascular Endothelial Growth Factors Proteins 0.000 claims 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 2
- 229960000397 bevacizumab Drugs 0.000 claims 2
- 229960002949 fluorouracil Drugs 0.000 claims 2
- 125000001188 haloalkyl group Chemical group 0.000 claims 2
- 150000004677 hydrates Chemical class 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 229940095102 methyl benzoate Drugs 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- 229960001592 paclitaxel Drugs 0.000 claims 2
- 206010041823 squamous cell carcinoma Diseases 0.000 claims 2
- RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 claims 2
- BSXVIJWHAJJGQP-QUCCMNQESA-N (1S,3R)-1-cyclohexyl-2-[(2-methylpropan-2-yl)oxycarbonyl]-1,3,4,9-tetrahydropyrido[3,4-b]indole-3-carboxylic acid Chemical compound C1([C@H]2C3=C(C4=CC=CC=C4N3)C[C@@H](N2C(=O)OC(C)(C)C)C(O)=O)CCCCC1 BSXVIJWHAJJGQP-QUCCMNQESA-N 0.000 claims 1
- ZLAJKSCIINOCQJ-QGZVFWFLSA-N (1r)-1-(1,3-benzodioxol-5-yl)-2,3,4,9-tetrahydro-1h-pyrido[3,4-b]indole Chemical compound N1C2=CC=CC=C2C(CCN2)=C1[C@H]2C1=CC=C2OCOC2=C1 ZLAJKSCIINOCQJ-QGZVFWFLSA-N 0.000 claims 1
- ICLWDXKTBLXCTH-GDLZYMKVSA-N (1r)-1-(1,3-benzodioxol-5-yl)-n-(naphthalen-1-ylmethyl)-1,3,4,9-tetrahydropyrido[3,4-b]indole-2-carbothioamide Chemical compound C1=C2OCOC2=CC([C@@H]2C3=C(C4=CC=CC=C4N3)CCN2C(NCC=2C3=CC=CC=C3C=CC=2)=S)=C1 ICLWDXKTBLXCTH-GDLZYMKVSA-N 0.000 claims 1
- HIAANGVNROVQOP-WGDIFIGCSA-N (1r)-1-(1,3-benzodioxol-5-yl)-n-[(1r)-1-phenylethyl]-1,3,4,9-tetrahydropyrido[3,4-b]indole-2-carboxamide Chemical compound C1([C@H](NC(=O)N2[C@@H](C3=C(C4=CC=CC=C4N3)CC2)C=2C=C3OCOC3=CC=2)C)=CC=CC=C1 HIAANGVNROVQOP-WGDIFIGCSA-N 0.000 claims 1
- FCTUDCYZEVZPCT-MRDQGFSESA-N (1r)-1-(1,3-benzodioxol-5-yl)-n-[(1s)-1-phenylethyl]-1,3,4,9-tetrahydropyrido[3,4-b]indole-2-carbothioamide Chemical compound C1([C@@H](NC(=S)N2[C@@H](C3=C(C4=CC=CC=C4N3)CC2)C=2C=C3OCOC3=CC=2)C)=CC=CC=C1 FCTUDCYZEVZPCT-MRDQGFSESA-N 0.000 claims 1
- HIAANGVNROVQOP-MRDQGFSESA-N (1r)-1-(1,3-benzodioxol-5-yl)-n-[(1s)-1-phenylethyl]-1,3,4,9-tetrahydropyrido[3,4-b]indole-2-carboxamide Chemical compound C1([C@@H](NC(=O)N2[C@@H](C3=C(C4=CC=CC=C4N3)CC2)C=2C=C3OCOC3=CC=2)C)=CC=CC=C1 HIAANGVNROVQOP-MRDQGFSESA-N 0.000 claims 1
- RKBZRWJUVUCBMG-RUZDIDTESA-N (1r)-1-(1,3-benzodioxol-5-yl)-n-[(2,4-dichlorophenyl)methyl]-1,3,4,9-tetrahydropyrido[3,4-b]indole-2-carbothioamide Chemical compound ClC1=CC(Cl)=CC=C1CNC(=S)N1[C@H](C=2C=C3OCOC3=CC=2)C(NC=2C3=CC=CC=2)=C3CC1 RKBZRWJUVUCBMG-RUZDIDTESA-N 0.000 claims 1
- HIXAHXZLKDRXQG-RUZDIDTESA-N (1r)-1-(1,3-benzodioxol-5-yl)-n-[(2-chlorophenyl)methyl]-1,3,4,9-tetrahydropyrido[3,4-b]indole-2-carbothioamide Chemical compound ClC1=CC=CC=C1CNC(=S)N1[C@H](C=2C=C3OCOC3=CC=2)C(NC=2C3=CC=CC=2)=C3CC1 HIXAHXZLKDRXQG-RUZDIDTESA-N 0.000 claims 1
- DJSLPVWDQVXUQC-RUZDIDTESA-N (1r)-1-(1,3-benzodioxol-5-yl)-n-[(2-fluorophenyl)methyl]-1,3,4,9-tetrahydropyrido[3,4-b]indole-2-carbothioamide Chemical compound FC1=CC=CC=C1CNC(=S)N1[C@H](C=2C=C3OCOC3=CC=2)C(NC=2C3=CC=CC=2)=C3CC1 DJSLPVWDQVXUQC-RUZDIDTESA-N 0.000 claims 1
- YZRYWRKTJJEVOQ-RUZDIDTESA-N (1r)-1-(1,3-benzodioxol-5-yl)-n-[(3,4-dichlorophenyl)methyl]-1,3,4,9-tetrahydropyrido[3,4-b]indole-2-carbothioamide Chemical compound C1=C(Cl)C(Cl)=CC=C1CNC(=S)N1[C@H](C=2C=C3OCOC3=CC=2)C(NC=2C3=CC=CC=2)=C3CC1 YZRYWRKTJJEVOQ-RUZDIDTESA-N 0.000 claims 1
- GPMVKRRMNJVBAV-HHHXNRCGSA-N (1r)-1-(1,3-benzodioxol-5-yl)-n-[(3,4-dimethylphenyl)methyl]-1,3,4,9-tetrahydropyrido[3,4-b]indole-2-carbothioamide Chemical compound C1=C(C)C(C)=CC=C1CNC(=S)N1[C@H](C=2C=C3OCOC3=CC=2)C(NC=2C3=CC=CC=2)=C3CC1 GPMVKRRMNJVBAV-HHHXNRCGSA-N 0.000 claims 1
- OIXNPIMNBDXGES-RUZDIDTESA-N (1r)-1-(1,3-benzodioxol-5-yl)-n-[(3-chlorophenyl)methyl]-1,3,4,9-tetrahydropyrido[3,4-b]indole-2-carbothioamide Chemical compound ClC1=CC=CC(CNC(=S)N2[C@@H](C3=C(C4=CC=CC=C4N3)CC2)C=2C=C3OCOC3=CC=2)=C1 OIXNPIMNBDXGES-RUZDIDTESA-N 0.000 claims 1
- YWTTYKPCIBCMBK-RUZDIDTESA-N (1r)-1-(1,3-benzodioxol-5-yl)-n-[(3-fluorophenyl)methyl]-1,3,4,9-tetrahydropyrido[3,4-b]indole-2-carbothioamide Chemical compound FC1=CC=CC(CNC(=S)N2[C@@H](C3=C(C4=CC=CC=C4N3)CC2)C=2C=C3OCOC3=CC=2)=C1 YWTTYKPCIBCMBK-RUZDIDTESA-N 0.000 claims 1
- YIWLWUWPQLALHS-RUZDIDTESA-N (1r)-1-(1,3-benzodioxol-5-yl)-n-[(4-chlorophenyl)methyl]-1,3,4,9-tetrahydropyrido[3,4-b]indole-2-carbothioamide Chemical compound C1=CC(Cl)=CC=C1CNC(=S)N1[C@H](C=2C=C3OCOC3=CC=2)C(NC=2C3=CC=CC=2)=C3CC1 YIWLWUWPQLALHS-RUZDIDTESA-N 0.000 claims 1
- GZUXRGTWMZUJHK-RUZDIDTESA-N (1r)-1-(1,3-benzodioxol-5-yl)-n-[(4-fluorophenyl)methyl]-1,3,4,9-tetrahydropyrido[3,4-b]indole-2-carbothioamide Chemical compound C1=CC(F)=CC=C1CNC(=S)N1[C@H](C=2C=C3OCOC3=CC=2)C(NC=2C3=CC=CC=2)=C3CC1 GZUXRGTWMZUJHK-RUZDIDTESA-N 0.000 claims 1
- BJUQSFREQWFYGV-XMMPIXPASA-N (1r)-1-(1,3-benzodioxol-5-yl)-n-[4-chloro-3-(trifluoromethyl)phenyl]-1,3,4,9-tetrahydropyrido[3,4-b]indole-2-carbothioamide Chemical compound C1=C(Cl)C(C(F)(F)F)=CC(NC(=S)N2[C@@H](C3=C(C4=CC=CC=C4N3)CC2)C=2C=C3OCOC3=CC=2)=C1 BJUQSFREQWFYGV-XMMPIXPASA-N 0.000 claims 1
- IGUHFPZEHYDZFF-XMMPIXPASA-N (1r)-1-(1,3-benzodioxol-5-yl)-n-benzoyl-1,3,4,9-tetrahydropyrido[3,4-b]indole-2-carboxamide Chemical compound N1([C@@H](C2=C(C3=CC=CC=C3N2)CC1)C=1C=C2OCOC2=CC=1)C(=O)NC(=O)C1=CC=CC=C1 IGUHFPZEHYDZFF-XMMPIXPASA-N 0.000 claims 1
- QYGADCBDUOXXRX-RUZDIDTESA-N (1r)-1-(1,3-benzodioxol-5-yl)-n-benzyl-1,3,4,9-tetrahydropyrido[3,4-b]indole-2-carbothioamide Chemical compound N1([C@@H](C2=C(C3=CC=CC=C3N2)CC1)C=1C=C2OCOC2=CC=1)C(=S)NCC1=CC=CC=C1 QYGADCBDUOXXRX-RUZDIDTESA-N 0.000 claims 1
- CVINNAYRKIJZES-RUZDIDTESA-N (1r)-1-(1,3-benzodioxol-5-yl)-n-benzyl-1,3,4,9-tetrahydropyrido[3,4-b]indole-2-carboxamide Chemical compound N1([C@@H](C2=C(C3=CC=CC=C3N2)CC1)C=1C=C2OCOC2=CC=1)C(=O)NCC1=CC=CC=C1 CVINNAYRKIJZES-RUZDIDTESA-N 0.000 claims 1
- MYPJGLGSGOSPMB-GGAORHGYSA-N (1s,3r)-1-(1-methylindol-3-yl)-2-[(2-methylpropan-2-yl)oxycarbonyl]-1,3,4,9-tetrahydropyrido[3,4-b]indole-3-carboxylic acid Chemical compound C12=CC=CC=C2N(C)C=C1[C@H]1C(NC=2C3=CC=CC=2)=C3C[C@H](C(O)=O)N1C(=O)OC(C)(C)C MYPJGLGSGOSPMB-GGAORHGYSA-N 0.000 claims 1
- WHCSUGSPORWTAH-IRLDBZIGSA-N (1s,3r)-1-(1h-indol-3-yl)-2-[(2-methylpropan-2-yl)oxycarbonyl]-1,3,4,9-tetrahydropyrido[3,4-b]indole-3-carboxylic acid Chemical compound C1=CC=C2C([C@H]3C4=C(C5=CC=CC=C5N4)C[C@@H](N3C(=O)OC(C)(C)C)C(O)=O)=CNC2=C1 WHCSUGSPORWTAH-IRLDBZIGSA-N 0.000 claims 1
- JQVYGRHHEWFKNA-PKTZIBPZSA-N (1s,3r)-n-[(4-chlorophenyl)methyl]-1-(2,4-dichlorophenyl)-2,3,4,9-tetrahydro-1h-pyrido[3,4-b]indole-3-carboxamide Chemical compound C1=CC(Cl)=CC=C1CNC(=O)[C@@H]1N[C@@H](C=2C(=CC(Cl)=CC=2)Cl)C(NC=2C3=CC=CC=2)=C3C1 JQVYGRHHEWFKNA-PKTZIBPZSA-N 0.000 claims 1
- GTXSRFUZSLTDFX-HRCADAONSA-N (2s)-n-[(2s)-3,3-dimethyl-1-(methylamino)-1-oxobutan-2-yl]-4-methyl-2-[[(2s)-2-sulfanyl-4-(3,4,4-trimethyl-2,5-dioxoimidazolidin-1-yl)butanoyl]amino]pentanamide Chemical compound CNC(=O)[C@H](C(C)(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](S)CCN1C(=O)N(C)C(C)(C)C1=O GTXSRFUZSLTDFX-HRCADAONSA-N 0.000 claims 1
- AUESVFAJZOFHTF-UHFFFAOYSA-N (3,4-difluorophenyl)-(1-phenyl-1,3,4,9-tetrahydropyrido[3,4-b]indol-2-yl)methanone Chemical compound C1=C(F)C(F)=CC=C1C(=O)N1C(C=2C=CC=CC=2)C(NC=2C3=CC=CC=2)=C3CC1 AUESVFAJZOFHTF-UHFFFAOYSA-N 0.000 claims 1
- IFVJWDIARFZZKC-SCBLGKRXSA-N (3r)-1-(1-benzylindol-3-yl)-2-[(2-methylpropan-2-yl)oxycarbonyl]-1,3,4,9-tetrahydropyrido[3,4-b]indole-3-carboxylic acid Chemical compound C([C@@H](N1C(=O)OC(C)(C)C)C(O)=O)C(C2=CC=CC=C2N2)=C2C1C(C1=CC=CC=C11)=CN1CC1=CC=CC=C1 IFVJWDIARFZZKC-SCBLGKRXSA-N 0.000 claims 1
- DCKKOHKSLCBUED-RMVMEJTISA-N (3r)-1-(1-butylindol-3-yl)-2-[(2-methylpropan-2-yl)oxycarbonyl]-1,3,4,9-tetrahydropyrido[3,4-b]indole-3-carboxylic acid Chemical compound C12=CC=CC=C2N(CCCC)C=C1C1C(NC=2C3=CC=CC=2)=C3C[C@H](C(O)=O)N1C(=O)OC(C)(C)C DCKKOHKSLCBUED-RMVMEJTISA-N 0.000 claims 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 125000006587 (C5-C10) heteroarylene group Chemical group 0.000 claims 1
- OICIUFXGPRSWNZ-UHFFFAOYSA-N 1-(1,3,4,9-tetrahydropyrido[3,4-b]indol-2-yl)ethanone Chemical compound N1C2=CC=CC=C2C2=C1CN(C(=O)C)CC2 OICIUFXGPRSWNZ-UHFFFAOYSA-N 0.000 claims 1
- QYGADCBDUOXXRX-UHFFFAOYSA-N 1-(1,3-benzodioxol-5-yl)-n-benzyl-1,3,4,9-tetrahydropyrido[3,4-b]indole-2-carbothioamide Chemical compound C1CC(C2=CC=CC=C2N2)=C2C(C=2C=C3OCOC3=CC=2)N1C(=S)NCC1=CC=CC=C1 QYGADCBDUOXXRX-UHFFFAOYSA-N 0.000 claims 1
- RZUGSCHPHUSQFH-UHFFFAOYSA-N 1-(1,3-benzodioxol-5-yl)-n-cyclohexyl-1,3,4,9-tetrahydropyrido[3,4-b]indole-2-carboxamide Chemical compound C1CC(C2=CC=CC=C2N2)=C2C(C=2C=C3OCOC3=CC=2)N1C(=O)NC1CCCCC1 RZUGSCHPHUSQFH-UHFFFAOYSA-N 0.000 claims 1
- HBCCVMZERHBAKW-UHFFFAOYSA-N 1-(1,3-benzodioxol-5-yl)-n-phenyl-1,3,4,9-tetrahydropyrido[3,4-b]indole-2-carboxamide Chemical compound C1CC(C2=CC=CC=C2N2)=C2C(C=2C=C3OCOC3=CC=2)N1C(=O)NC1=CC=CC=C1 HBCCVMZERHBAKW-UHFFFAOYSA-N 0.000 claims 1
- SSLNFDGKAGXRFX-UHFFFAOYSA-N 1-(2,4-dimethoxyphenyl)-2,3,4,9-tetrahydro-1h-pyrido[3,4-b]indole Chemical compound COC1=CC(OC)=CC=C1C1C(NC=2C3=CC=CC=2)=C3CCN1 SSLNFDGKAGXRFX-UHFFFAOYSA-N 0.000 claims 1
- LVEUORKAEYEUPQ-UHFFFAOYSA-N 1-(2,5-dimethoxyphenyl)-2,3,4,9-tetrahydro-1h-pyrido[3,4-b]indole Chemical compound COC1=CC=C(OC)C(C2C3=C(C4=CC=CC=C4N3)CCN2)=C1 LVEUORKAEYEUPQ-UHFFFAOYSA-N 0.000 claims 1
- YPOUKKHERCNHSK-UHFFFAOYSA-N 1-(3,4,5-trimethoxyphenyl)-2,3,4,9-tetrahydro-1h-pyrido[3,4-b]indole Chemical compound COC1=C(OC)C(OC)=CC(C2C3=C(C4=CC=CC=C4N3)CCN2)=C1 YPOUKKHERCNHSK-UHFFFAOYSA-N 0.000 claims 1
- ROOBULYVOVIYRW-UHFFFAOYSA-N 1-(3,4-dimethoxyphenyl)-2,3,4,9-tetrahydro-1h-pyrido[3,4-b]indole Chemical compound C1=C(OC)C(OC)=CC=C1C1C(NC=2C3=CC=CC=2)=C3CCN1 ROOBULYVOVIYRW-UHFFFAOYSA-N 0.000 claims 1
- DCNKZXPWASLNNH-UHFFFAOYSA-N 1-(3,5-dimethoxyphenyl)-2,3,4,9-tetrahydro-1h-pyrido[3,4-b]indole Chemical compound COC1=CC(OC)=CC(C2C3=C(C4=CC=CC=C4N3)CCN2)=C1 DCNKZXPWASLNNH-UHFFFAOYSA-N 0.000 claims 1
- WGYYSMJOWKKZPO-UHFFFAOYSA-N 1-(3-chloro-4-methoxyphenyl)-n-phenyl-1,3,4,9-tetrahydropyrido[3,4-b]indole-2-carboxamide Chemical compound C1=C(Cl)C(OC)=CC=C1C1C(NC=2C3=CC=CC=2)=C3CCN1C(=O)NC1=CC=CC=C1 WGYYSMJOWKKZPO-UHFFFAOYSA-N 0.000 claims 1
- HPHJFDGJKPJDGN-UHFFFAOYSA-N 1-(4-bromophenyl)-2,3,4,9-tetrahydro-1h-pyrido[3,4-b]indole Chemical compound C1=CC(Br)=CC=C1C1C(NC=2C3=CC=CC=2)=C3CCN1 HPHJFDGJKPJDGN-UHFFFAOYSA-N 0.000 claims 1
- ILKMFTINEKPIRM-UHFFFAOYSA-N 1-(4-chlorophenyl)-2,3,4,9-tetrahydro-1h-pyrido[3,4-b]indole Chemical compound C1=CC(Cl)=CC=C1C1C(NC=2C3=CC=CC=2)=C3CCN1 ILKMFTINEKPIRM-UHFFFAOYSA-N 0.000 claims 1
- UZUVPSXDEVELNB-UHFFFAOYSA-N 1-(4-nitro-1,3-benzodioxol-5-yl)-2,3,4,9-tetrahydro-1h-pyrido[3,4-b]indole Chemical compound N1C2=CC=CC=C2C(CCN2)=C1C2C1=CC=C2OCOC2=C1[N+](=O)[O-] UZUVPSXDEVELNB-UHFFFAOYSA-N 0.000 claims 1
- GTZHXBQPFWAUOT-UHFFFAOYSA-N 1-(4-nitrophenyl)-2,3,4,9-tetrahydro-1h-pyrido[3,4-b]indole Chemical compound C1=CC([N+](=O)[O-])=CC=C1C1C(NC=2C3=CC=CC=2)=C3CCN1 GTZHXBQPFWAUOT-UHFFFAOYSA-N 0.000 claims 1
- ASSWMQPRKRHWSP-UHFFFAOYSA-N 1-(9-ethylcarbazol-3-yl)-2,3,4,9-tetrahydro-1h-pyrido[3,4-b]indole Chemical compound N1C2=CC=CC=C2C(CCN2)=C1C2C1=CC=C2N(CC)C3=CC=CC=C3C2=C1 ASSWMQPRKRHWSP-UHFFFAOYSA-N 0.000 claims 1
- JLJKYIUEHZAHGL-UHFFFAOYSA-N 1-(9h-fluoren-2-yl)-2,3,4,9-tetrahydro-1h-pyrido[3,4-b]indole Chemical compound N1C2=CC=CC=C2C(CCN2)=C1C2C1=CC=C2C3=CC=CC=C3CC2=C1 JLJKYIUEHZAHGL-UHFFFAOYSA-N 0.000 claims 1
- INERHEQVAVQJBO-UHFFFAOYSA-N 1-phenyl-2,3,4,9-tetrahydro-1h-pyrido[3,4-b]indole Chemical compound N1CCC(C2=CC=CC=C2N2)=C2C1C1=CC=CC=C1 INERHEQVAVQJBO-UHFFFAOYSA-N 0.000 claims 1
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| EP1604011A4 (en) | 2003-01-21 | 2009-12-09 | Ptc Therapeutics Inc | METHODS FOR IDENTIFYING COMPOUNDS THAT MODULATE THE EXPRESSION OF DEPENDENT GENES FROM A NON-TRANSLATED REGION, AND METHODS OF USING SAME |
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| US8076352B2 (en) * | 2004-03-15 | 2011-12-13 | Ptc Therapeutics, Inc. | Administration of carboline derivatives useful in the treatment of cancer and other diseases |
| US8168591B2 (en) * | 2005-10-17 | 2012-05-01 | The Regents Of The University Of California | Compositions and methods related to anti-FGF agents |
| US20070258976A1 (en) * | 2006-05-04 | 2007-11-08 | Ward Keith W | Combination Therapy for Diseases Involving Angiogenesis |
| WO2008103470A2 (en) * | 2007-02-21 | 2008-08-28 | Trustees Of Columbia University In The City Of New York | Oncogenic-ras-signal dependent lethal compounds |
| CA2683444A1 (en) * | 2007-04-13 | 2008-10-23 | Ptc Therapeutics, Inc. | Administration of carboline derivatives useful in the treatment of cancer and other diseases |
| US8283115B1 (en) | 2007-06-20 | 2012-10-09 | Ptc Therapeutics, Inc. | Methods of screening for compounds for treating muscular dystrophy using UTRN mRNA translation regulation |
| US8283116B1 (en) | 2007-06-22 | 2012-10-09 | Ptc Therapeutics, Inc. | Methods of screening for compounds for treating spinal muscular atrophy using SMN mRNA translation regulation |
| CN105777776B (zh) * | 2007-08-29 | 2021-06-08 | 梅特希尔基因公司 | 蛋白酪氨酸激酶活性的抑制剂 |
| US11202775B2 (en) * | 2007-09-25 | 2021-12-21 | Minerva Biotechnologies Corporation | Methods for treatment of cancer |
| WO2010138695A1 (en) * | 2009-05-27 | 2010-12-02 | Ptc Therapeutics, Inc. | Methods for treating neurofibromatosis |
| US8703726B2 (en) | 2009-05-27 | 2014-04-22 | Ptc Therapeutics, Inc. | Methods for treating prostate conditions |
| MX2011012517A (es) * | 2009-05-27 | 2012-01-27 | Ptc Therapeutics Inc | Procesos para la preparacion de tetrahidro beta - carbolina sustituidas. |
| US8697662B2 (en) | 2009-05-27 | 2014-04-15 | Ptc Therapeutics, Inc. | Methods for treating Kaposi sarcoma |
| US9351964B2 (en) | 2009-05-27 | 2016-05-31 | Ptc Therapeutics, Inc. | Methods for treating cancer and non-neoplastic conditions |
| US20120157402A1 (en) * | 2009-05-27 | 2012-06-21 | Liangxian Cao | Methods for treating brain tumors |
| WO2011063223A1 (en) * | 2009-11-20 | 2011-05-26 | Southern Research Institute | TETRAHYDRO-β-CARBOLINE DERIVATIVES, SYNTHESIS AND USE THEREOF |
| WO2011150162A1 (en) * | 2010-05-27 | 2011-12-01 | Ptc Therapeutics, Inc. | Methods for treating viral conditions |
| PT2688569T (pt) | 2011-03-21 | 2018-08-06 | Vivolux Ab | Tratamento de tumores sólidos |
| US20130116219A1 (en) * | 2011-11-04 | 2013-05-09 | Alcon Research, Ltd. | Antimicrobial carboline compounds |
| ES2734479T3 (es) | 2012-09-21 | 2019-12-10 | Vivolux Ab | Medios y métodos para tratar tumores sólidos |
| MX2015014666A (es) | 2013-04-17 | 2016-03-01 | Pfizer | Derivados de n-piperidin-3-ilbenzamida para tratar enfermedades cardiovasculares. |
| US10307406B2 (en) * | 2013-08-31 | 2019-06-04 | The Wistar Institute Of Anatomy And Biology | Methods and compositions for re-activating Epstein-Barr virus and screening compounds therefor |
| BR112016030690B1 (pt) * | 2014-06-27 | 2023-11-14 | Nogra Pharma Limited | Compostos moduladores do receptor de arila, composição farmacêutica compreendendo os mesmos e usos terapêuticos dos ditos compostos |
| NZ769496A (en) | 2014-12-18 | 2023-09-29 | Hoffmann La Roche | Tetrahydro-pyrido[3,4-b]indole estrogen receptor modulators and uses thereof |
| CN108513537A (zh) * | 2015-09-23 | 2018-09-07 | 米纳瓦生物技术公司 | 筛选分化干细胞的试剂的方法 |
| IL310489A (en) | 2015-10-01 | 2024-03-01 | Olema Pharmaceuticals Inc | TETRAHYDRO-1H-PYRIDO[3,4-b]INDOLE ANTI-ESTROGENIC DRUGS AND COMPOSITIONS COMPRISING SAME FOR USE IN TREATING CANCER |
| US20180002344A1 (en) | 2016-06-16 | 2018-01-04 | Genentech, Inc. | Heteroaryl estrogen receptor modulators and uses thereof |
| KR20200035292A (ko) | 2017-08-01 | 2020-04-02 | 피티씨 테라퓨틱스, 인크. | 혈액 암 치료에 사용하기 위한 dhodh 억제제 |
| AU2018367909B2 (en) | 2017-11-17 | 2022-03-10 | Cellix Bio Private Limited | Compositions and methods for the treatment of eye disorders |
| KR102564647B1 (ko) | 2018-06-21 | 2023-08-11 | 에프. 호프만-라 로슈 아게 | 3-((1R,3R)-1-(2,6-다이플루오로-4-((1-(3-플루오로프로필)아제티딘-3-일)아미노)페닐)-3-메틸-1,3,4,9-테트라하이드로-2H-피리도[3,4-b]인돌-2-일)-2,2-다이플루오로프로판-1-올의 고체 형태, 치환된 페닐 또는 피리딘일 잔기를 포함하는 융합된 삼환형 화합물의 제조 방법, 및 이의 사용 방법 |
| EP3829544A1 (en) | 2018-08-03 | 2021-06-09 | PTC Therapeutics, Inc. | Bioavailable oral dosage forms |
| BR112021002630A2 (pt) | 2018-08-17 | 2021-05-11 | Ptc Therapeutics, Inc. | método para tratar câncer pancreático |
| EP3860996A4 (en) | 2018-10-02 | 2022-08-31 | Northwestern University | BETA-CARBOLINES AS POSITIVE ALLOSTERIC MODULATORS OF HUMAN SEROTONIN RECEPTOR 2C (5-HT2C) |
| US20220096473A1 (en) | 2019-01-15 | 2022-03-31 | Ptc Therapeutics, Inc. | Method for treating an acute myeloid leukemia |
| MX2022000279A (es) | 2019-07-07 | 2022-02-03 | Olema Pharmaceuticals Inc | Regimenes de antagonistas del receptor de estrogeno. |
| JP2024502270A (ja) | 2020-12-23 | 2024-01-18 | リキュリウム アイピー ホールディングス リミテッド ライアビリティー カンパニー | エストロゲン受容体調節薬 |
| IL313144A (en) * | 2021-12-31 | 2024-07-01 | Ptc Therapeutics Inc | Carboline compounds and use thereof |
Family Cites Families (106)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3492304A (en) * | 1968-06-24 | 1970-01-27 | Warner Lambert Pharmaceutical | 5,6,7,7a,8,8a,9,10,12,12a-decahydro-11h-benz(b)indolo(3,2,1-ij) 1,5 naphthyridin-11-ones |
| US4014890A (en) * | 1976-03-23 | 1977-03-29 | Pfizer Inc. | Process for preparing indole derivatives |
| FR2432025A1 (fr) | 1978-07-28 | 1980-02-22 | Synthelabo | Derives d'imidazo et de pyrimido-pyrido-indoles, leur preparation et leur application en therapeutique |
| EP0008249B1 (fr) | 1978-07-28 | 1981-08-26 | Synthelabo | Dérivés de fluorènes et fluoranthènes, leur procédé de préparation et leur application en thérapeutique |
| FR2575753B1 (fr) * | 1985-01-07 | 1987-02-20 | Adir | Nouveaux derives peptidiques a structure polycyclique azotee, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| US5039801A (en) | 1985-12-20 | 1991-08-13 | The United States Of America As Represented By The Department Of Health & Human Services | Thermal fragmentation of methylbenzylurea disastereomers or secondary amines and preparation of optically active secondary amines |
| US4754038A (en) * | 1987-02-26 | 1988-06-28 | American Home Products Corporation | Carboline histamine H1 antagonists |
| EP0300541B1 (en) | 1987-07-20 | 1996-03-27 | Duphar International Research B.V | 8,9-anellated-1,2,3,4-tetrahydro-beta-carboline derivatives |
| EP0357122A3 (en) * | 1988-08-29 | 1991-10-23 | Duphar International Research B.V | Use of beta-carbolines, their bio-isosteric benzofuran and benzothiophene analogues for the manufacture of a medicament having cytostatic properties |
| US5166170A (en) | 1989-07-03 | 1992-11-24 | Hoechst-Roussel Pharmaceuticals Incorporated | 2-(aminoaryl) indoles and indolines as topical antiinflammatory agents for the treatment of skin disorders |
| US5166204A (en) * | 1989-11-01 | 1992-11-24 | Toyama Chemical Co., Ltd. | Isoindole derivatives and salts thereof and antitumor agent comprising the same |
| US5120543A (en) | 1989-12-21 | 1992-06-09 | The United States Of America As Represented By The Secretary Of Agriculture | Molluscicidal β-carboline carboxylic acids and methods using the same |
| JPH03287586A (ja) | 1990-04-02 | 1991-12-18 | Taisho Pharmaceut Co Ltd | テトラヒドロ―β―カルボリン誘導体 |
| FR2662940B1 (fr) | 1990-06-08 | 1994-10-14 | Roussel Uclaf | Utilisation de derives de la tetrahydro isoquinoleine pour la preparation de medicaments anti-tumoraux, application a titre de medicaments de derives de la tetrahydro isoquinoleine et produits derives de cette structure. |
| US5162336A (en) | 1990-06-21 | 1992-11-10 | Rhone-Poulenc Rorer Pharmaceuticals Inc. | Tetrahydro-pyrido-indoles as cholecystokinin and gastrin antagonists |
| US5187180A (en) | 1990-07-26 | 1993-02-16 | Merck Frosst Canada, Inc. | (quinolin-2-ylmethoxy)heterotetrahydrocarbazoles as inhibitors of the biosynthesis of leukotrienes |
| JPH04275221A (ja) | 1991-03-01 | 1992-09-30 | Taisho Pharmaceut Co Ltd | 制癌効果増強剤 |
| US5382569A (en) * | 1991-05-16 | 1995-01-17 | Warner-Lambert Company | Endotherlin antagonists |
| JP3287586B2 (ja) | 1991-07-09 | 2002-06-04 | キヤノン株式会社 | カラー画像処理方法、及びカラー画像処理装置 |
| US5206377A (en) | 1991-12-05 | 1993-04-27 | Whitby Research, Inc. | Compounds useful as antiproliferative agents |
| US5622960A (en) | 1992-04-14 | 1997-04-22 | The United States Of America As Represented By The Department Of Health And Human Services | Topoisomerase II inhibitors and therapeutic uses therefor |
| US5314898A (en) | 1992-06-29 | 1994-05-24 | Merck & Co., Inc. | Aryl thiopyrano[4,3,2-cd]indoles as inhibitors of leukotriene biosynthesis |
| US5314900A (en) | 1992-11-19 | 1994-05-24 | Merck Frosst Canada, Inc. | Aryl thiopyrano[2,3,4-C,D]indoles as inhibitors of leukotriene biosynthesis |
| US6824976B1 (en) * | 1993-04-02 | 2004-11-30 | Rigel Pharmaceuticals, Inc. | Method for selective inactivation of viral replication |
| EP0620222A3 (en) | 1993-04-14 | 1995-04-12 | Lilly Co Eli | Tetrahydro-beta-carbolines. |
| US5403851A (en) * | 1994-04-05 | 1995-04-04 | Interneuron Pharmaceuticals, Inc. | Substituted tryptamines, phenalkylamines and related compounds |
| US5451600A (en) * | 1994-04-19 | 1995-09-19 | Hoffmann-La Roche Inc. | Substituted tetrahydrobenzopyrrolylfuranoic acid derivatives as phospholipase A2 inhibitors |
| FR2724384B1 (fr) | 1994-09-14 | 1999-04-16 | Cemaf | Nouveaux derives de la 3,4-dihydro beta-carboline agonistes de la melatonine, leur procede de preparation et leur utilisation a titre de medicament |
| US5663309A (en) | 1994-12-12 | 1997-09-02 | Ciba-Geigy Corporation | Diazo dyes having a phenylene group as the middle component and a naphthalene group as the terminal diazo component |
| IL117208A0 (en) | 1995-02-23 | 1996-06-18 | Nissan Chemical Ind Ltd | Indole type thiazolidines |
| US6376529B1 (en) * | 1995-06-07 | 2002-04-23 | Peng Cho Tang | Mono- and bis-indolylquinones and prophylactic and therapeutic uses thereof |
| GB9514473D0 (en) | 1995-07-14 | 1995-09-13 | Glaxo Lab Sa | Chemical compounds |
| US5633388A (en) * | 1996-03-29 | 1997-05-27 | Viropharma Incorporated | Compounds, compositions and methods for treatment of hepatitis C |
| KR20000005175A (ko) * | 1996-04-04 | 2000-01-25 | 프리돌린 클라우스너, 롤란드 비. 보레르 | 테트라하이드로-베타-카르볼린 유도체의 항전이제로서의 용도 |
| FR2748026B1 (fr) * | 1996-04-26 | 1998-06-05 | Adir | Nouveaux inhibiteurs de metalloproteases, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| CZ358598A3 (cs) | 1996-05-10 | 1999-03-17 | Icos Corporation | Karbolinové deriváty |
| US6013633A (en) * | 1997-08-07 | 2000-01-11 | University Of Cincinnati | Compounds for control of appetite, blood pressure, cardiovascular response, libido, and circadian rhythm |
| US5892041A (en) * | 1996-08-12 | 1999-04-06 | Neurogen Corporation | Fused indolecarboxamides: dopamine receptor subtype specific ligands |
| US6331543B1 (en) | 1996-11-01 | 2001-12-18 | Nitromed, Inc. | Nitrosated and nitrosylated phosphodiesterase inhibitors, compositions and methods of use |
| US6653132B1 (en) * | 1997-02-25 | 2003-11-25 | Qbi Enterprises, Ltd. | IRES sequences with high translational efficiency and expression vectors containing the sequence |
| US6043252A (en) | 1997-05-05 | 2000-03-28 | Icos Corporation | Carboline derivatives |
| AR016133A1 (es) | 1997-07-31 | 2001-06-20 | Wyeth Corp | Compuesto de carbamiloxi que inhiben la adhesion de leucocitos mediada por vla-4, compuestos que son prodrogas de dichos compuestos, composicionfarmaceutica, metodo para fijar vla-4 a una muestra biologica, metodo para el tratamiento de una condicion inflamatoria |
| US6514981B1 (en) * | 1998-04-02 | 2003-02-04 | Sugen, Inc. | Methods of modulating tyrosine protein kinase function with indolinone compounds |
| JP4275221B2 (ja) | 1998-07-06 | 2009-06-10 | リンテック株式会社 | 粘接着剤組成物および粘接着シート |
| GB9828709D0 (en) | 1998-12-24 | 1999-02-17 | Novartis Ag | Assay |
| US6548493B1 (en) | 1999-06-15 | 2003-04-15 | Bristol-Myers Squibb Pharma Company | Substituted heterocycle fused gamma-carbolines |
| FR2796644B1 (fr) | 1999-07-23 | 2001-09-07 | Adir | Nouveaux derives de beta-carboline, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| GB9918962D0 (en) * | 1999-08-11 | 1999-10-13 | Cerebrus Ltd | Chemical compounds xxii |
| US20020016298A1 (en) * | 1999-09-01 | 2002-02-07 | Hay Bruce A. | Somatostatin antagonists and agonists that act at the sst subtype 2 receptor |
| US6696418B1 (en) * | 1999-09-01 | 2004-02-24 | Pfizer Inc. | Somatostatin antagonists and agonists that act at the SST subtype 2 receptor |
| PT1214292E (pt) | 1999-09-24 | 2007-09-14 | Genentech Inc | Derivados de tirosina |
| DE19962936A1 (de) | 1999-12-24 | 2001-06-28 | Bayer Ag | Neue beta-Aminosäureverbindungen als Integrinantagonisten |
| US6890933B1 (en) | 2000-02-24 | 2005-05-10 | President And Fellows Of Harvard College | Kinesin inhibitors |
| UA74826C2 (en) | 2000-05-17 | 2006-02-15 | Ortho Mcneil Pharm Inc | ?-carboline derivatives as phosphodiesterase inhibitors |
| UA72611C2 (uk) | 2000-05-17 | 2005-03-15 | Орто-Макнейл Фармацевтикал, Інк. | Похідні заміщеного піролопіридинону, корисні як інгібітори фосфодіестерази |
| US6630638B1 (en) * | 2000-05-26 | 2003-10-07 | Abb Inc. | Dead tank drawout breakers |
| US7498304B2 (en) | 2000-06-16 | 2009-03-03 | Curis, Inc. | Angiogenesis-modulating compositions and uses |
| US20030158168A1 (en) | 2000-08-09 | 2003-08-21 | Giorgio Massimini | Composition for combined use of aromatase inhibitors |
| US6720330B2 (en) | 2000-11-17 | 2004-04-13 | Pfizer Inc. | Somatostatin antagonists and agonists that act at the SST subtype 2 receptor |
| US6849619B2 (en) * | 2000-12-20 | 2005-02-01 | Bristol-Myers Squibb Company | Substituted pyridoindoles as serotonin agonists and antagonists |
| BR0116429A (pt) | 2000-12-20 | 2006-05-09 | Bristol Myers Squibb Co | piridoindóis substituìdos como agonistas e antagonistas da serotonina |
| CA2433100A1 (en) | 2000-12-27 | 2002-07-04 | Helmut Haning | Indole derivatives as ligands of thyroid receptors |
| US7122554B2 (en) * | 2001-02-12 | 2006-10-17 | Lilly Icos Llc. | Carboline derivatives |
| WO2002077609A2 (en) * | 2001-03-26 | 2002-10-03 | Message Pharmaceuticals, Inc. | Identification of compounds for the treatment or prevention of proliferative diseases |
| US6720331B2 (en) * | 2001-04-03 | 2004-04-13 | National Sun Yat-Sen University | 1-substituted 1,2,3,4-tetrahydro-β-carboline and 3,4-dihydro-β-carboline and analogs as antitumor agents |
| US7115621B2 (en) | 2001-04-25 | 2006-10-03 | Lilly Icos Llc | Chemical compounds |
| EP2329822A1 (en) | 2001-09-05 | 2011-06-08 | Minerva Biotechnologies Corporation | Compositions and methods of treatment of cancer |
| ES2278064T3 (es) * | 2001-10-19 | 2007-08-01 | Transtech Pharma Inc. | Derivados de beta-carbolina como inhibidores de ptp. |
| US20030130171A1 (en) | 2001-10-30 | 2003-07-10 | Schoenhard Grant L. | Inhibitors of ABC drug transporters in multidrug resistant microbial cells |
| KR20040068240A (ko) | 2001-12-14 | 2004-07-30 | 노보 노르디스크 에이/에스 | 호르몬 민감성 리파아제의 활성을 감소시키기 위한 화합물및 그들의 사용 |
| EP1348434A1 (en) | 2002-03-27 | 2003-10-01 | Fujisawa Deutschland GmbH | Use of pyridyl amides as inhibitors of angiogenesis |
| WO2003087815A2 (en) | 2002-04-17 | 2003-10-23 | Novartis Ag | Method for the identification of inhibitors of the binding of are-containing mrn a and an hur protein |
| US20030220377A1 (en) * | 2002-05-08 | 2003-11-27 | Richard Chesworth | Indole compounds and their use as estrogen agonists/antagonists |
| TWI329111B (en) | 2002-05-24 | 2010-08-21 | X Ceptor Therapeutics Inc | Azepinoindole and pyridoindole derivatives as pharmaceutical agents |
| US7595311B2 (en) | 2002-05-24 | 2009-09-29 | Exelixis, Inc. | Azepinoindole derivatives as pharmaceutical agents |
| CN1658855B (zh) | 2002-06-06 | 2010-04-28 | 株式会社医药分子设计研究所 | O-取代羟基芳基衍生物 |
| ATE344030T1 (de) | 2002-10-18 | 2006-11-15 | Hoffmann La Roche | 4-piperazinylbenzolsulfonyl-indole mit 5-ht6 rezeptor-affinität |
| US8426194B2 (en) * | 2003-01-21 | 2013-04-23 | Ptc Therapeutics, Inc. | Methods and agents for screening for compounds capable of modulating VEGF expression |
| WO2004069831A1 (en) | 2003-02-10 | 2004-08-19 | Glenmark Pharmaceuticals Ltd. | Tricyclic compounds useful for the treatment of inflammatory and allergic disorders: process for their preparation |
| AU2003902023A0 (en) | 2003-04-29 | 2003-05-15 | The Australian National University | A method of indole synthesis |
| GB0311201D0 (en) | 2003-05-15 | 2003-06-18 | Merck Sharp & Dohme | Therapeutic agents |
| US7351733B2 (en) | 2003-06-10 | 2008-04-01 | Smithkline Beecham Corporation | Tetrahydrocarbazole derivatives and their pharmaceutical use |
| BRPI0411245A (pt) | 2003-06-12 | 2006-07-18 | Smithkline Beecham Corp | composto, composição farmacêutica, uso de um composto, e, métodos para tratamento ou profilaxia de vìrus oncogênicos e para tratamento ou profilaxia de condições ou distúrbios devidos a infecção por hpv |
| US20060235012A1 (en) | 2003-06-16 | 2006-10-19 | Chroma Therapeutics Limited | Carboline and betacarboline derivatives for use as hdac enzyme inhibitors |
| MXPA05013922A (es) | 2003-06-20 | 2006-02-24 | Coley Pharm Group Inc | Antagonistas de receptor tipo toll de molecula pequena. |
| EP1637521B1 (en) | 2003-06-23 | 2013-06-19 | Ono Pharmaceutical Co., Ltd. | Novel tricyclic heterocycle compound |
| WO2005000244A2 (en) | 2003-06-25 | 2005-01-06 | Elan Pharmaceuticals, Inc. | Methods and compositions for treating rheumatoid arthritis |
| US20050143371A1 (en) | 2003-07-23 | 2005-06-30 | Pharmacia Corporation | Beta-carboline compounds and analogues thereof as mitogen-activated protein kinase-activated protein kinase-2 inhibitors |
| WO2005014543A1 (ja) | 2003-08-06 | 2005-02-17 | Japan Tobacco Inc. | 縮合環化合物及びそのｈｃｖポリメラーゼ阻害剤としての利用 |
| US7491794B2 (en) | 2003-10-14 | 2009-02-17 | Intermune, Inc. | Macrocyclic compounds as inhibitors of viral replication |
| EP1678137A1 (en) | 2003-10-15 | 2006-07-12 | Chiron Corporation | Compositions and methods for viral inhibition |
| AU2005206570A1 (en) | 2004-01-23 | 2005-08-04 | Novartis Vaccines And Diagnostics, Inc. | Tetrahydrocarboline compounds as anticancer agents |
| US20080103213A1 (en) | 2004-03-05 | 2008-05-01 | Board Of Regents, The University Of Texas System | Liposomal curcumin for treatment of neurofibromatosis |
| EP1737461B1 (en) * | 2004-03-15 | 2012-12-12 | PTC Therapeutics, Inc. | Carboline derivatives useful in the inhibition of angiogenesis |
| US8940896B2 (en) * | 2004-03-15 | 2015-01-27 | Ptc Therapeutics, Inc. | Tetra-cyclic carboline derivatives useful in the inhibition of angiogenesis |
| US8076352B2 (en) * | 2004-03-15 | 2011-12-13 | Ptc Therapeutics, Inc. | Administration of carboline derivatives useful in the treatment of cancer and other diseases |
| US7767689B2 (en) | 2004-03-15 | 2010-08-03 | Ptc Therapeutics, Inc. | Carboline derivatives useful in the treatment of cancer |
| US8076353B2 (en) * | 2004-03-15 | 2011-12-13 | Ptc Therapeutics, Inc. | Inhibition of VEGF translation |
| EP1763361A2 (en) | 2004-04-01 | 2007-03-21 | Elan Pharmaceuticals, Inc. | Steroid sparing agents and their use |
| JP2007532681A (ja) | 2004-04-16 | 2007-11-15 | ジェネンテック・インコーポレーテッド | Ｂ細胞の枯渇を増大させる方法 |
| FR2869540B1 (fr) * | 2004-04-30 | 2008-05-16 | Centre Nat Rech Scient Cnrse | Compositions pharmaceutiques contenant des derives de b-carboline, et leur utilisation pour le traitement des cancers |
| JP2008506683A (ja) | 2004-07-18 | 2008-03-06 | コーリー ファーマシューティカル グループ， リミテッド | 先天免疫応答を誘導するための方法および組成物 |
| EP1786425A1 (en) | 2004-08-02 | 2007-05-23 | SmithKline Beecham Corporation | Useful compounds for hpv infection |
| CA2588607A1 (en) * | 2004-11-23 | 2006-06-01 | Ptc Therapeutics, Inc. | Carbazole, carboline and indole derivatives useful in the inhibition of vegf production |
| WO2008128100A1 (en) | 2007-04-13 | 2008-10-23 | The Regents Of The University Of California | Small-molecule inhibitors of the androgen receptor |
| CA2683444A1 (en) | 2007-04-13 | 2008-10-23 | Ptc Therapeutics, Inc. | Administration of carboline derivatives useful in the treatment of cancer and other diseases |
-
2005
- 2005-04-18 US US11/107,783 patent/US7767689B2/en not_active Expired - Fee Related
-
2006
- 2006-04-17 WO PCT/US2006/014547 patent/WO2006113703A2/en not_active Ceased
- 2006-04-17 JP JP2008506824A patent/JP2008536876A/ja active Pending
- 2006-04-17 EP EP11150082A patent/EP2298304A3/en not_active Withdrawn
- 2006-04-17 EP EP06750554A patent/EP1871375B1/en not_active Not-in-force
- 2006-04-17 AT AT06750554T patent/ATE547102T1/de active
-
2010
- 2010-03-02 US US12/715,651 patent/US8372860B2/en not_active Expired - Fee Related
-
2011
- 2011-03-04 US US13/040,614 patent/US20110160190A1/en not_active Abandoned
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