NZ588388A - Carboline derivatives useful in the inhibition of angiogenesis - Google Patents
Carboline derivatives useful in the inhibition of angiogenesisInfo
- Publication number
- NZ588388A NZ588388A NZ588388A NZ58838805A NZ588388A NZ 588388 A NZ588388 A NZ 588388A NZ 588388 A NZ588388 A NZ 588388A NZ 58838805 A NZ58838805 A NZ 58838805A NZ 588388 A NZ588388 A NZ 588388A
- Authority
- NZ
- New Zealand
- Prior art keywords
- optionally substituted
- iponz
- received
- mar
- alkyl
- Prior art date
Links
- 230000014399 negative regulation of angiogenesis Effects 0.000 title abstract description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 52
- 125000000217 alkyl group Chemical group 0.000 claims description 53
- 125000003545 alkoxy group Chemical group 0.000 claims description 37
- 229910052736 halogen Inorganic materials 0.000 claims description 36
- 150000002367 halogens Chemical group 0.000 claims description 36
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 31
- 125000003118 aryl group Chemical group 0.000 claims description 30
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 22
- 125000001424 substituent group Chemical group 0.000 claims description 21
- -1 amino, morpholinyl Chemical group 0.000 claims description 18
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 18
- 125000003282 alkyl amino group Chemical group 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 14
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 11
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 11
- 125000002757 morpholinyl group Chemical group 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 125000004193 piperazinyl group Chemical group 0.000 claims description 7
- 125000003386 piperidinyl group Chemical group 0.000 claims description 7
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 6
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 6
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 125000000304 alkynyl group Chemical group 0.000 claims description 6
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 125000000466 oxiranyl group Chemical group 0.000 claims description 5
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 5
- 150000003536 tetrazoles Chemical class 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 4
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 4
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 4
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 4
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 3
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 claims description 3
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 3
- 229930192474 thiophene Natural products 0.000 claims description 3
- QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 claims description 2
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims description 2
- 102000005789 Vascular Endothelial Growth Factors Human genes 0.000 abstract description 53
- 108010019530 Vascular Endothelial Growth Factors Proteins 0.000 abstract description 53
- 206010028980 Neoplasm Diseases 0.000 abstract description 33
- 201000011510 cancer Diseases 0.000 abstract description 22
- 230000005764 inhibitory process Effects 0.000 abstract description 15
- 230000014509 gene expression Effects 0.000 abstract description 13
- 238000000034 method Methods 0.000 abstract description 13
- 206010012689 Diabetic retinopathy Diseases 0.000 abstract description 10
- 208000002780 macular degeneration Diseases 0.000 abstract description 10
- 230000006711 vascular endothelial growth factor production Effects 0.000 abstract description 8
- 239000000460 chlorine Substances 0.000 description 165
- 108010073929 Vascular Endothelial Growth Factor A Proteins 0.000 description 53
- 125000000623 heterocyclic group Chemical group 0.000 description 27
- 125000001072 heteroaryl group Chemical group 0.000 description 17
- 125000005842 heteroatom Chemical group 0.000 description 12
- 230000033115 angiogenesis Effects 0.000 description 11
- 210000004027 cell Anatomy 0.000 description 9
- 230000000694 effects Effects 0.000 description 8
- 206010021143 Hypoxia Diseases 0.000 description 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 230000004614 tumor growth Effects 0.000 description 7
- 108010053099 Vascular Endothelial Growth Factor Receptor-2 Proteins 0.000 description 6
- 102100033177 Vascular endothelial growth factor receptor 2 Human genes 0.000 description 6
- 125000003277 amino group Chemical group 0.000 description 6
- 208000037976 chronic inflammation Diseases 0.000 description 6
- 230000006020 chronic inflammation Effects 0.000 description 6
- 230000002401 inhibitory effect Effects 0.000 description 6
- 125000004043 oxo group Chemical group O=* 0.000 description 6
- 108020003175 receptors Proteins 0.000 description 6
- 102000005962 receptors Human genes 0.000 description 6
- 108020004459 Small interfering RNA Proteins 0.000 description 5
- 238000013459 approach Methods 0.000 description 5
- 125000004429 atom Chemical group 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 201000010099 disease Diseases 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 description 4
- 208000005590 Choroidal Neovascularization Diseases 0.000 description 4
- 206010060823 Choroidal neovascularisation Diseases 0.000 description 4
- 241000699660 Mus musculus Species 0.000 description 4
- 206010029113 Neovascularisation Diseases 0.000 description 4
- 208000007135 Retinal Neovascularization Diseases 0.000 description 4
- 108091008605 VEGF receptors Proteins 0.000 description 4
- 230000001594 aberrant effect Effects 0.000 description 4
- 230000010261 cell growth Effects 0.000 description 4
- 239000003102 growth factor Substances 0.000 description 4
- 230000007954 hypoxia Effects 0.000 description 4
- 230000001404 mediated effect Effects 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 108090000623 proteins and genes Proteins 0.000 description 4
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- 230000005747 tumor angiogenesis Effects 0.000 description 4
- 229940121358 tyrosine kinase inhibitor Drugs 0.000 description 4
- 239000005483 tyrosine kinase inhibitor Substances 0.000 description 4
- 201000001320 Atherosclerosis Diseases 0.000 description 3
- 108090000695 Cytokines Proteins 0.000 description 3
- 102000004127 Cytokines Human genes 0.000 description 3
- 208000008589 Obesity Diseases 0.000 description 3
- 201000004681 Psoriasis Diseases 0.000 description 3
- 125000004414 alkyl thio group Chemical group 0.000 description 3
- 239000002870 angiogenesis inducing agent Substances 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 230000018109 developmental process Effects 0.000 description 3
- 208000037765 diseases and disorders Diseases 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 210000002889 endothelial cell Anatomy 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 238000011580 nude mouse model Methods 0.000 description 3
- 235000020824 obesity Nutrition 0.000 description 3
- 230000008506 pathogenesis Effects 0.000 description 3
- 230000001023 pro-angiogenic effect Effects 0.000 description 3
- 230000001105 regulatory effect Effects 0.000 description 3
- 206010039073 rheumatoid arthritis Diseases 0.000 description 3
- 230000007998 vessel formation Effects 0.000 description 3
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 description 2
- FTNJQNQLEGKTGD-UHFFFAOYSA-N 1,3-benzodioxole Chemical compound C1=CC=C2OCOC2=C1 FTNJQNQLEGKTGD-UHFFFAOYSA-N 0.000 description 2
- 108020005345 3' Untranslated Regions Proteins 0.000 description 2
- 108020003589 5' Untranslated Regions Proteins 0.000 description 2
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 102000053642 Catalytic RNA Human genes 0.000 description 2
- 108090000994 Catalytic RNA Proteins 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- 102000003974 Fibroblast growth factor 2 Human genes 0.000 description 2
- 108090000379 Fibroblast growth factor 2 Proteins 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- 108020004684 Internal Ribosome Entry Sites Proteins 0.000 description 2
- 108091034117 Oligonucleotide Proteins 0.000 description 2
- 108700020796 Oncogene Proteins 0.000 description 2
- 108010029485 Protein Isoforms Proteins 0.000 description 2
- 102000001708 Protein Isoforms Human genes 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 108010053096 Vascular Endothelial Growth Factor Receptor-1 Proteins 0.000 description 2
- 102100033178 Vascular endothelial growth factor receptor 1 Human genes 0.000 description 2
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 2
- 206010064930 age-related macular degeneration Diseases 0.000 description 2
- 230000001772 anti-angiogenic effect Effects 0.000 description 2
- 230000000692 anti-sense effect Effects 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
- 230000004663 cell proliferation Effects 0.000 description 2
- 230000002596 correlated effect Effects 0.000 description 2
- 208000035475 disorder Diseases 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 238000007876 drug discovery Methods 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 125000002541 furyl group Chemical group 0.000 description 2
- 125000001188 haloalkyl group Chemical group 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 230000001146 hypoxic effect Effects 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
- 108020004999 messenger RNA Proteins 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- 210000002307 prostate Anatomy 0.000 description 2
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 2
- 230000002207 retinal effect Effects 0.000 description 2
- 108091092562 ribozyme Proteins 0.000 description 2
- 230000019491 signal transduction Effects 0.000 description 2
- 230000011664 signaling Effects 0.000 description 2
- 239000003270 steroid hormone Substances 0.000 description 2
- 125000004434 sulfur atom Chemical group 0.000 description 2
- 230000008685 targeting Effects 0.000 description 2
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 description 2
- 210000001519 tissue Anatomy 0.000 description 2
- 238000013519 translation Methods 0.000 description 2
- 230000014621 translational initiation Effects 0.000 description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- 108091032973 (ribonucleotides)n+m Proteins 0.000 description 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- FYADHXFMURLYQI-UHFFFAOYSA-N 1,2,4-triazine Chemical compound C1=CN=NC=N1 FYADHXFMURLYQI-UHFFFAOYSA-N 0.000 description 1
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 description 1
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
- BJHCYTJNPVGSBZ-YXSASFKJSA-N 1-[4-[6-amino-5-[(Z)-methoxyiminomethyl]pyrimidin-4-yl]oxy-2-chlorophenyl]-3-ethylurea Chemical compound CCNC(=O)Nc1ccc(Oc2ncnc(N)c2\C=N/OC)cc1Cl BJHCYTJNPVGSBZ-YXSASFKJSA-N 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
- DQQNMIPXXNPGCV-UHFFFAOYSA-N 3-hexyne Chemical compound CCC#CCC DQQNMIPXXNPGCV-UHFFFAOYSA-N 0.000 description 1
- 108091023037 Aptamer Proteins 0.000 description 1
- 201000004569 Blindness Diseases 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 101100296726 Caenorhabditis elegans pde-5 gene Proteins 0.000 description 1
- 201000009030 Carcinoma Diseases 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 206010061818 Disease progression Diseases 0.000 description 1
- 108010041308 Endothelial Growth Factors Proteins 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 206010018338 Glioma Diseases 0.000 description 1
- 102000004269 Granulocyte Colony-Stimulating Factor Human genes 0.000 description 1
- 108010017080 Granulocyte Colony-Stimulating Factor Proteins 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- 241001562081 Ikeda Species 0.000 description 1
- 102000004218 Insulin-Like Growth Factor I Human genes 0.000 description 1
- 108090000723 Insulin-Like Growth Factor I Proteins 0.000 description 1
- 241001529936 Murinae Species 0.000 description 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical group C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 1
- 229910005849 NiNx Inorganic materials 0.000 description 1
- 102000043276 Oncogene Human genes 0.000 description 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
- 241000288906 Primates Species 0.000 description 1
- 102000004022 Protein-Tyrosine Kinases Human genes 0.000 description 1
- 108090000412 Protein-Tyrosine Kinases Proteins 0.000 description 1
- 108091027981 Response element Proteins 0.000 description 1
- 206010038848 Retinal detachment Diseases 0.000 description 1
- 206010038933 Retinopathy of prematurity Diseases 0.000 description 1
- 241000283984 Rodentia Species 0.000 description 1
- 206010039491 Sarcoma Diseases 0.000 description 1
- 108091023040 Transcription factor Proteins 0.000 description 1
- 102000040945 Transcription factor Human genes 0.000 description 1
- 102000009618 Transforming Growth Factors Human genes 0.000 description 1
- 108010009583 Transforming Growth Factors Proteins 0.000 description 1
- 108060008682 Tumor Necrosis Factor Proteins 0.000 description 1
- 102000044209 Tumor Suppressor Genes Human genes 0.000 description 1
- 108700025716 Tumor Suppressor Genes Proteins 0.000 description 1
- 102100040247 Tumor necrosis factor Human genes 0.000 description 1
- 101150049278 US20 gene Proteins 0.000 description 1
- 102000009524 Vascular Endothelial Growth Factor A Human genes 0.000 description 1
- 102000016549 Vascular Endothelial Growth Factor Receptor-2 Human genes 0.000 description 1
- 125000004103 aminoalkyl group Chemical group 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
- 230000003527 anti-angiogenesis Effects 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 229910052789 astatine Inorganic materials 0.000 description 1
- RYXHOMYVWAEKHL-UHFFFAOYSA-N astatine atom Chemical compound [At] RYXHOMYVWAEKHL-UHFFFAOYSA-N 0.000 description 1
- 125000003828 azulenyl group Chemical group 0.000 description 1
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 description 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 125000001589 carboacyl group Chemical group 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 230000024245 cell differentiation Effects 0.000 description 1
- 210000003986 cell retinal photoreceptor Anatomy 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 239000013256 coordination polymer Substances 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 125000004982 dihaloalkyl group Chemical group 0.000 description 1
- 230000005750 disease progression Effects 0.000 description 1
- 210000001671 embryonic stem cell Anatomy 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- JKFAIQOWCVVSKC-UHFFFAOYSA-N furazan Chemical compound C=1C=NON=1 JKFAIQOWCVVSKC-UHFFFAOYSA-N 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 230000001631 hypertensive effect Effects 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 208000026278 immune system disease Diseases 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 230000002779 inactivation Effects 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 208000027866 inflammatory disease Diseases 0.000 description 1
- 230000002757 inflammatory effect Effects 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 230000000302 ischemic effect Effects 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002605 large molecules Chemical class 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 230000003211 malignant effect Effects 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 210000004088 microvessel Anatomy 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- 238000010172 mouse model Methods 0.000 description 1
- 230000035772 mutation Effects 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 239000002547 new drug Substances 0.000 description 1
- 108020004707 nucleic acids Proteins 0.000 description 1
- 102000039446 nucleic acids Human genes 0.000 description 1
- 150000007523 nucleic acids Chemical class 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000002018 overexpression Effects 0.000 description 1
- 238000012261 overproduction Methods 0.000 description 1
- 125000003566 oxetanyl group Chemical group 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 230000007170 pathology Effects 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
- 230000000649 photocoagulation Effects 0.000 description 1
- 238000010837 poor prognosis Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- 239000002464 receptor antagonist Substances 0.000 description 1
- 229940044551 receptor antagonist Drugs 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 238000007634 remodeling Methods 0.000 description 1
- 230000004264 retinal detachment Effects 0.000 description 1
- 210000000844 retinal pigment epithelial cell Anatomy 0.000 description 1
- 108091008601 sVEGFR Proteins 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 229960003080 taurine Drugs 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000004853 tetrahydropyridinyl group Chemical group N1(CCCC=C1)* 0.000 description 1
- 125000003507 tetrahydrothiofenyl group Chemical group 0.000 description 1
- 125000004632 tetrahydrothiopyranyl group Chemical group S1C(CCCC1)* 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 238000013518 transcription Methods 0.000 description 1
- 230000035897 transcription Effects 0.000 description 1
- 238000011830 transgenic mouse model Methods 0.000 description 1
- 125000004385 trihaloalkyl group Chemical group 0.000 description 1
- 210000004881 tumor cell Anatomy 0.000 description 1
- 150000004917 tyrosine kinase inhibitor derivatives Chemical class 0.000 description 1
- 230000003827 upregulation Effects 0.000 description 1
- 238000010200 validation analysis Methods 0.000 description 1
- 210000003556 vascular endothelial cell Anatomy 0.000 description 1
- 230000008728 vascular permeability Effects 0.000 description 1
- 239000002525 vasculotropin inhibitor Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
- A61K31/437—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/4738—Quinolines; Isoquinolines ortho- or peri-condensed with heterocyclic ring systems
- A61K31/4745—Quinolines; Isoquinolines ortho- or peri-condensed with heterocyclic ring systems condensed with ring systems having nitrogen as a ring hetero atom, e.g. phenantrolines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/4965—Non-condensed pyrazines
- A61K31/497—Non-condensed pyrazines containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A61K31/5355—Non-condensed oxazines and containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/54—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame
- A61K31/541—Non-condensed thiazines containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
- A61K31/551—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole having two nitrogen atoms, e.g. dilazep
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Ophthalmology & Optometry (AREA)
- Rheumatology (AREA)
- Child & Adolescent Psychology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Pain & Pain Management (AREA)
- Urology & Nephrology (AREA)
- Dermatology (AREA)
- Vascular Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyrrole Compounds (AREA)
- Developing Agents For Electrophotography (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US55272504P | 2004-03-15 | 2004-03-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NZ588388A true NZ588388A (en) | 2012-05-25 |
Family
ID=34963165
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NZ588388A NZ588388A (en) | 2004-03-15 | 2005-03-15 | Carboline derivatives useful in the inhibition of angiogenesis |
Country Status (22)
| Country | Link |
|---|---|
| US (2) | US7601840B2 (https=) |
| EP (2) | EP1737461B1 (https=) |
| JP (2) | JP4857452B2 (https=) |
| KR (2) | KR20120073287A (https=) |
| CN (2) | CN1980672B (https=) |
| AU (1) | AU2005222632B2 (https=) |
| BR (1) | BRPI0508814B8 (https=) |
| CA (1) | CA2559408C (https=) |
| DK (1) | DK1737461T3 (https=) |
| EA (2) | EA016575B1 (https=) |
| EC (1) | ECSP066928A (https=) |
| ES (1) | ES2401335T3 (https=) |
| IL (1) | IL178079A (https=) |
| MX (1) | MXPA06010543A (https=) |
| NO (1) | NO338270B1 (https=) |
| NZ (1) | NZ588388A (https=) |
| PL (1) | PL1737461T3 (https=) |
| PT (1) | PT1737461E (https=) |
| SG (2) | SG184755A1 (https=) |
| UA (1) | UA92317C2 (https=) |
| WO (1) | WO2005089764A1 (https=) |
| ZA (1) | ZA200608176B (https=) |
Families Citing this family (62)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9068234B2 (en) * | 2003-01-21 | 2015-06-30 | Ptc Therapeutics, Inc. | Methods and agents for screening for compounds capable of modulating gene expression |
| US8426194B2 (en) * | 2003-01-21 | 2013-04-23 | Ptc Therapeutics, Inc. | Methods and agents for screening for compounds capable of modulating VEGF expression |
| US8460864B2 (en) | 2003-01-21 | 2013-06-11 | Ptc Therapeutics, Inc. | Methods for identifying compounds that modulate untranslated region-dependent gene expression and methods of using same |
| ES2427166T3 (es) | 2003-06-23 | 2013-10-29 | Ono Pharmaceutical Co., Ltd. | Compuesto heterocíclico tricíclico novedoso |
| US8076352B2 (en) * | 2004-03-15 | 2011-12-13 | Ptc Therapeutics, Inc. | Administration of carboline derivatives useful in the treatment of cancer and other diseases |
| MXPA06010543A (es) | 2004-03-15 | 2007-03-26 | Ptc Therapeutics Inc | Derivados de carbolina utiles en la inhibicion de la angiogenesis. |
| 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 |
| US20080103164A1 (en) * | 2004-08-02 | 2008-05-01 | Kristjan Gudmundsson | Useful compounds for hpv infection |
| WO2006068164A1 (ja) | 2004-12-22 | 2006-06-29 | Ono Pharmaceutical Co., Ltd. | 三環式化合物およびその用途 |
| WO2007002051A1 (en) * | 2005-06-22 | 2007-01-04 | Smithkline Beecham Corporation | Carboline derivatives and their use as inhibitors of flaviviridae infections |
| ITMI20061581A1 (it) * | 2006-08-04 | 2008-02-05 | Univ Bari | Ligandi del recettore beta-3 adrenergico e loro uso in terapia |
| WO2008103470A2 (en) * | 2007-02-21 | 2008-08-28 | Trustees Of Columbia University In The City Of New York | Oncogenic-ras-signal dependent lethal compounds |
| US8642067B2 (en) | 2007-04-02 | 2014-02-04 | Allergen, Inc. | Methods and compositions for intraocular administration to treat ocular conditions |
| 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 |
| US11202775B2 (en) | 2007-09-25 | 2021-12-21 | Minerva Biotechnologies Corporation | Methods for treatment of cancer |
| WO2009042815A1 (en) * | 2007-09-25 | 2009-04-02 | Minerva Biotechnologies Corp. | Methods for treatment of cancer |
| US20120157401A1 (en) * | 2009-05-27 | 2012-06-21 | Ptc Therapeutics, Inc. | Methods for treating neurofibromatosis |
| MX2011012517A (es) * | 2009-05-27 | 2012-01-27 | Ptc Therapeutics Inc | Procesos para la preparacion de tetrahidro beta - carbolina sustituidas. |
| MX373926B (es) | 2009-05-27 | 2020-07-10 | Ptc Therapeutics Inc | Metodos para tratar cancer y estados no neoplasicos. |
| WO2010138685A1 (en) * | 2009-05-27 | 2010-12-02 | Ptc Therapeutics, Inc. | Methods for treating prostate conditions |
| US8697662B2 (en) | 2009-05-27 | 2014-04-15 | Ptc Therapeutics, Inc. | Methods for treating Kaposi sarcoma |
| 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 |
| CN102250127B (zh) * | 2010-05-19 | 2013-06-19 | 首都医科大学 | 两个氨基酸修饰的四氢咔啉衍生物及其制备方法和应用 |
| JP5649170B2 (ja) * | 2010-11-26 | 2015-01-07 | 国立大学法人 千葉大学 | テトラヒドロ−β−カルボリン誘導体及びその製造方法 |
| CN102424681B (zh) * | 2011-10-24 | 2014-10-15 | 华东师范大学 | 酰基四氢-β-咔啉类化合物及其衍生物、用途及其制备方法 |
| WO2013067409A1 (en) * | 2011-11-04 | 2013-05-10 | Alcon Research, Ltd. | Antimicrobial carboline compounds |
| WO2014089177A2 (en) | 2012-12-04 | 2014-06-12 | Massachusetts Institute Of Technology | Compounds, conjugates and compositions of epipolythiodiketopiperazines and polythiodiketopiperazines |
| 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 |
| CN111978319B (zh) | 2014-06-27 | 2023-08-11 | 诺格拉制药有限公司 | 芳基受体调制剂及其制备和使用方法 |
| KR102785474B1 (ko) * | 2014-12-18 | 2025-03-26 | 에프. 호프만-라 로슈 아게 | 테트라하이드로-피리도[3,4-b]인돌 에스트로겐 수용체 조절제 및 이의 용도 |
| WO2016187767A1 (en) * | 2015-05-25 | 2016-12-01 | Hutchison Medipharma Limited | Pharmaceutical compositions and use thereof |
| JP2019515643A (ja) * | 2015-09-23 | 2019-06-13 | ミネルバ バイオテクノロジーズ コーポレーション | 幹細胞分化剤のスクリーニング方法 |
| KR102710603B1 (ko) * | 2015-10-01 | 2024-09-27 | 올레마 파마슈티컬스 인코포레이티드 | 테트라히드로-1H-피리도[3,4-b]인돌 항에스트로겐 약물 |
| CN105330665B (zh) * | 2015-11-04 | 2017-10-03 | 衡阳师范学院 | 一种抑制激肽释放酶klk7的化合物、制备方法和用途 |
| CN109362222B (zh) * | 2016-02-05 | 2021-03-19 | 益方生物科技(上海)股份有限公司 | 选择性雌激素受体降解物及其用途 |
| US10918627B2 (en) | 2016-05-11 | 2021-02-16 | Massachusetts Institute Of Technology | Convergent and enantioselective total synthesis of Communesin analogs |
| JP7018026B2 (ja) * | 2016-06-16 | 2022-02-09 | エフ・ホフマン－ラ・ロシュ・アクチェンゲゼルシャフト | ヘテロアリールエストロゲン受容体モジュレーター及びその使用 |
| US20180002344A1 (en) | 2016-06-16 | 2018-01-04 | Genentech, Inc. | Heteroaryl estrogen receptor modulators and uses thereof |
| WO2018209239A1 (en) | 2017-05-11 | 2018-11-15 | Massachusetts Institute Of Technology | Potent agelastatin derivatives as modulators for cancer invasion and metastasis |
| WO2019028171A1 (en) | 2017-08-01 | 2019-02-07 | Ptc Therapeutics, Inc. | DHODH INHIBITOR FOR USE IN THE TREATMENT OF HEMATOLOGICAL CANCERS |
| US10640508B2 (en) | 2017-10-13 | 2020-05-05 | Massachusetts Institute Of Technology | Diazene directed modular synthesis of compounds with quaternary carbon centers |
| CA3081553C (en) | 2017-11-17 | 2022-11-15 | Cellix Bio Private Limited | Compositions and methods for the treatment of eye disorders |
| LT3810283T (lt) | 2018-06-21 | 2023-08-25 | F. Hoffmann-La Roche Ag | 3-((1r,3r)-1-(2,6-difluor-4-((1-(3-fluorpropil)azetidin-3- il)amino) fenil)-3-metil-1,3,4,9-tetrahidro-2h-pirido[3,4-b]indol-2-il)- 2,2- difluorpropan-1-olio tartrato druskos kietosios formos, jų paruošimo procesas ir jų naudojimo būdai vėžiui gydyti |
| JP2021532193A (ja) | 2018-08-03 | 2021-11-25 | ピーティーシー セラピューティクス， インコーポレイテッド | 生物学的に利用可能な経口剤形 |
| CN113164479A (zh) | 2018-08-17 | 2021-07-23 | Ptc医疗公司 | 用于治疗胰腺癌的方法 |
| US11485734B2 (en) | 2018-10-02 | 2022-11-01 | Northwestern University | Beta-carbolines as positive allosteric modulators of the human serotonin receptor 2C (5-HT2C) |
| CN109400604B (zh) * | 2018-10-25 | 2021-09-03 | 河北科技大学 | 2,3,4,9-四氢-1H-吡啶并[3,4-b]吲哚类化合物及用途 |
| WO2020150326A1 (en) | 2019-01-15 | 2020-07-23 | Ptc Therapeutics, Inc. | Method for treating an acute myeloid leukemia |
| US11535634B2 (en) | 2019-06-05 | 2022-12-27 | Massachusetts Institute Of Technology | Compounds, conjugates, and compositions of epipolythiodiketopiperazines and polythiodiketopiperazines and uses thereof |
| MX2022000279A (es) | 2019-07-07 | 2022-02-03 | Olema Pharmaceuticals Inc | Regimenes de antagonistas del receptor de estrogeno. |
| CN110698474B (zh) * | 2019-11-14 | 2021-11-02 | 福州大学 | 一种α位取代四氢-γ-咔啉类化合物及其制备方法和应用 |
| CN113121527B (zh) * | 2019-12-31 | 2024-09-06 | 上海辉启生物医药科技有限公司 | 三环类化合物及其用途 |
| CN113546172A (zh) * | 2020-04-24 | 2021-10-26 | 山东大学齐鲁医院 | Vegf抑制剂在制备治疗缺氧相关疾病药物中的应用 |
| EP4267578A4 (en) | 2020-12-23 | 2024-11-20 | Recurium IP Holdings, LLC | ESTROGEN RECEPTOR MODULATORS |
| WO2022182415A1 (en) | 2021-02-24 | 2022-09-01 | Massachusetts Institute Of Technology | Himastatin derivatives, and processes of preparation thereof, and uses thereof |
| CA3237691A1 (en) * | 2021-12-31 | 2023-07-06 | Ptc Therapeutics, Inc. | Carboline compounds and use thereof |
| CN119654324A (zh) | 2022-08-05 | 2025-03-18 | 株式会社次代生物科学 | 作为缺氧诱导因子1（hif-1）抑制剂或血管内皮生长因子（vegf）抑制剂的新的化合物和包含其的药物组合物 |
| CN116375702B (zh) * | 2023-03-16 | 2025-06-17 | 贵州大学 | 一种含烷基或芳基的1，2，3，4-四氢-β-咔啉类化合物、组合物、制备方法和应用 |
| CN116531371A (zh) * | 2023-04-28 | 2023-08-04 | 中国人民解放军中部战区总医院 | 一类化合物在制备治疗与醛脱氢酶2活性相关的疾病或症状的药物中的用途 |
Family Cites Families (109)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1055203A (en) * | 1964-09-16 | 1967-01-18 | Ici Ltd | -ß-carboline derivatives, a process for their manufacture, and compositions containing them |
| 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 |
| ATE165T1 (de) | 1978-07-28 | 1981-09-15 | Synthelabo | Fluoren- und fluoranthenderivate, verfahren zu ihrer herstellung und ihre therapeutische verwendung. |
| 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 |
| US5500431A (en) * | 1993-04-14 | 1996-03-19 | Eli Lilly And Company | Tetrahydro-β-carbolines |
| 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 |
| DE69710182T2 (de) * | 1996-04-04 | 2002-08-29 | F. Hoffmann-La Roche Ag, Basel | Verwendung von tetrahydrobetacarbolin-derivaten zur vorbeugung der metastasenbildung |
| FR2748026B1 (fr) | 1996-04-26 | 1998-06-05 | Adir | Nouveaux inhibiteurs de metalloproteases, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| ES2175404T3 (es) * | 1996-05-10 | 2002-11-16 | Icos Corp | Derivados de carbolina. |
| 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 |
| WO1998037189A1 (en) * | 1997-02-25 | 1998-08-27 | 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 |
| MXPA01012969A (es) | 1999-06-15 | 2003-10-14 | Bristol Myers Squibb Pharma Co | Gamma-carbolinas fusionadas de heterociclo sustituido. |
| 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 |
| US6696418B1 (en) * | 1999-09-01 | 2004-02-24 | Pfizer Inc. | Somatostatin antagonists and agonists that act at the SST subtype 2 receptor |
| US20020016298A1 (en) * | 1999-09-01 | 2002-02-07 | Hay Bruce A. | Somatostatin antagonists and agonists that act at the sst subtype 2 receptor |
| CA2385882C (en) | 1999-09-24 | 2009-11-24 | Genentech, Inc. | Tyrosine derivatives |
| 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 |
| US7498304B2 (en) | 2000-06-16 | 2009-03-03 | Curis, Inc. | Angiogenesis-modulating compositions and uses |
| JP2004505909A (ja) | 2000-08-09 | 2004-02-26 | フアルマシア・イタリア・エツセ・ピー・アー | アロマターゼ阻害薬の併用型組成物 |
| US6720330B2 (en) * | 2000-11-17 | 2004-04-13 | Pfizer Inc. | Somatostatin antagonists and agonists that act at the SST subtype 2 receptor |
| EP1347759B1 (en) * | 2000-12-08 | 2005-06-29 | Smithkline Beecham Corporation | Antibacterial compounds |
| US6849619B2 (en) | 2000-12-20 | 2005-02-01 | Bristol-Myers Squibb Company | Substituted pyridoindoles as serotonin agonists and antagonists |
| PL366233A1 (en) | 2000-12-20 | 2005-01-24 | Bristol-Myers Squibb Company | Substituted pyridoindoles as serotonin agonists and antagonists |
| WO2002051805A1 (de) | 2000-12-27 | 2002-07-04 | Bayer Aktiengesellschaft | Indol-derivate |
| AU2002249890A1 (en) | 2001-02-12 | 2002-08-28 | Lilly Icos Llc | Carboline derivatives |
| JP4220779B2 (ja) * | 2001-02-12 | 2009-02-04 | リリー アイコス リミテッド ライアビリティ カンパニー | 化学化合物 |
| US6630589B1 (en) * | 2001-03-26 | 2003-10-07 | Message Pharmaceuticals | 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 |
| EP1383765B1 (en) | 2001-04-25 | 2006-12-13 | Lilly Icos LLC | Carboline derivatives as inhibitors of phosphodiesterase 5 (PDE5) for the treatment of cardiovascular diseases and erectile dysfunction |
| US6701957B2 (en) * | 2001-08-16 | 2004-03-09 | Fisher Controls International Llc | Fluid pressure reduction device |
| JP2005507876A (ja) | 2001-09-05 | 2005-03-24 | ミナーバ バイオテクノロジーズ コーポレイション | 癌を治療する組成物および方法 |
| ATE348828T1 (de) * | 2001-10-19 | 2007-01-15 | Transtech Pharma Inc | Beta-carbolin-derivate als ptp-inhibitoren |
| 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 |
| JP4328058B2 (ja) * | 2002-04-12 | 2009-09-09 | 株式会社エイ・エル・エイ | 糖尿病合併症を予防する組成物 |
| AU2003226820A1 (en) | 2002-04-17 | 2003-10-27 | 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 |
| US7595311B2 (en) | 2002-05-24 | 2009-09-29 | Exelixis, Inc. | Azepinoindole derivatives as pharmaceutical agents |
| TWI329111B (en) | 2002-05-24 | 2010-08-21 | X Ceptor Therapeutics Inc | Azepinoindole and pyridoindole derivatives as pharmaceutical agents |
| JP4743382B2 (ja) | 2002-06-06 | 2011-08-10 | 株式会社医薬分子設計研究所 | Ｏ−置換ヒドロキシアリール誘導体 |
| PL376479A1 (en) | 2002-10-18 | 2005-12-27 | F.Hoffmann-La Roche Ag | 4-piperazinyl benzenesulfonyl indoles with 5-ht6 receptor affinity |
| 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 |
| KR20060017545A (ko) | 2003-06-10 | 2006-02-23 | 스미스클라인 비참 코포레이션 | 테트라하이드로카르바졸 유도체 및 이들의 약제학적 용도 |
| DE602004022169D1 (de) | 2003-06-12 | 2009-09-03 | Smithkline Beecham Corp | Tetrahydrocarbazolderivate und deren pharmazeutische verwendung |
| US20060235012A1 (en) | 2003-06-16 | 2006-10-19 | Chroma Therapeutics Limited | Carboline and betacarboline derivatives for use as hdac enzyme inhibitors |
| BRPI0411514A (pt) | 2003-06-20 | 2006-08-01 | Coley Pharm Gmbh | antagonistas de receptor toll-like de molécula pequena |
| ES2427166T3 (es) | 2003-06-23 | 2013-10-29 | Ono Pharmaceutical Co., Ltd. | Compuesto heterocíclico tricíclico novedoso |
| AR044927A1 (es) | 2003-06-25 | 2005-10-12 | Elan Pharm Inc | Metodos y composiciones para tratar la artritis reumatoidea |
| US20050137220A1 (en) | 2003-07-23 | 2005-06-23 | 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 |
| JP2007509057A (ja) | 2003-10-15 | 2007-04-12 | カイロン コーポレイション | ウイルス阻害のための組成物および方法 |
| CN1910183A (zh) | 2004-01-23 | 2007-02-07 | 希龙公司 | 四氢咔啉化合物作为抗癌药 |
| US20080103213A1 (en) | 2004-03-05 | 2008-05-01 | Board Of Regents, The University Of Texas System | Liposomal curcumin for treatment of neurofibromatosis |
| US8076353B2 (en) | 2004-03-15 | 2011-12-13 | Ptc Therapeutics, Inc. | Inhibition of VEGF translation |
| 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 |
| MXPA06010543A (es) | 2004-03-15 | 2007-03-26 | Ptc Therapeutics Inc | Derivados de carbolina utiles en la inhibicion de la angiogenesis. |
| WO2005097162A2 (en) | 2004-04-01 | 2005-10-20 | Elan Pharmaceuticals, Inc. | Steroid sparing agents and their use |
| BRPI0508762A (pt) | 2004-04-16 | 2007-08-14 | Genentech Inc | método de aumento do esgotamento de células b em mamìferos, método de aumento da eficácia do esgotamento de células b, método de tratamento de malignidade ou neoplasma de células b, método de alìvio de disfunção autoimunológica regulada por células b, método de esgotamento das células b e composição |
| CA2574090A1 (en) | 2004-07-18 | 2006-12-21 | Coley Pharmaceutical Group, Ltd. | Methods and compositions for inducing innate immune responses |
| US20080103164A1 (en) | 2004-08-02 | 2008-05-01 | Kristjan Gudmundsson | Useful compounds for hpv infection |
| US8143257B2 (en) | 2004-11-23 | 2012-03-27 | Ptc Therapeutics, Inc. | Substituted phenols as active agents inhibiting VEGF production |
| WO2008128100A1 (en) | 2007-04-13 | 2008-10-23 | The Regents Of The University Of California | Small-molecule inhibitors of the androgen receptor |
| US20100158858A1 (en) | 2007-04-13 | 2010-06-24 | Liangxian Cao | Administration of carboline derivatives useful in the treatment of cancer and other diseases |
-
2005
- 2005-03-15 MX MXPA06010543A patent/MXPA06010543A/es active IP Right Grant
- 2005-03-15 SG SG2012068193A patent/SG184755A1/en unknown
- 2005-03-15 UA UAA200610306A patent/UA92317C2/ru unknown
- 2005-03-15 PT PT57255606T patent/PT1737461E/pt unknown
- 2005-03-15 ZA ZA200608176A patent/ZA200608176B/en unknown
- 2005-03-15 CA CA2559408A patent/CA2559408C/en not_active Expired - Fee Related
- 2005-03-15 EP EP05725560A patent/EP1737461B1/en not_active Expired - Lifetime
- 2005-03-15 CN CN2005800149439A patent/CN1980672B/zh not_active Expired - Fee Related
- 2005-03-15 EA EA200601697A patent/EA016575B1/ru unknown
- 2005-03-15 DK DK05725560.6T patent/DK1737461T3/da active
- 2005-03-15 KR KR1020127010279A patent/KR20120073287A/ko not_active Ceased
- 2005-03-15 EP EP11178488A patent/EP2431369A3/en not_active Withdrawn
- 2005-03-15 KR KR1020067021300A patent/KR101188778B1/ko not_active Expired - Fee Related
- 2005-03-15 BR BRPI0508814A patent/BRPI0508814B8/pt not_active IP Right Cessation
- 2005-03-15 WO PCT/US2005/008481 patent/WO2005089764A1/en not_active Ceased
- 2005-03-15 CN CN2011100576737A patent/CN102408425A/zh active Pending
- 2005-03-15 JP JP2007504011A patent/JP4857452B2/ja not_active Expired - Fee Related
- 2005-03-15 SG SG200901748-4A patent/SG151267A1/en unknown
- 2005-03-15 EA EA201200555A patent/EA201200555A1/ru unknown
- 2005-03-15 PL PL05725560T patent/PL1737461T3/pl unknown
- 2005-03-15 ES ES05725560T patent/ES2401335T3/es not_active Expired - Lifetime
- 2005-03-15 US US11/079,420 patent/US7601840B2/en active Active
- 2005-03-15 AU AU2005222632A patent/AU2005222632B2/en not_active Ceased
- 2005-03-15 NZ NZ588388A patent/NZ588388A/en not_active IP Right Cessation
-
2006
- 2006-09-14 IL IL178079A patent/IL178079A/en active IP Right Grant
- 2006-10-05 NO NO20064519A patent/NO338270B1/no unknown
- 2006-10-16 EC EC2006006928A patent/ECSP066928A/es unknown
-
2009
- 2009-07-21 US US12/506,485 patent/US8367694B2/en not_active Expired - Fee Related
-
2011
- 2011-07-25 JP JP2011162351A patent/JP2012012398A/ja active Pending
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| NZ588388A (en) | Carboline derivatives useful in the inhibition of angiogenesis | |
| US8372860B2 (en) | Carboline derivatives useful in the inhibition of angiogenesis | |
| EP1732543B1 (en) | Tetracyclic carboline deratives for inhibiting angiogenesis | |
| AU2012200474A1 (en) | Carboline derivatives useful in the inhibition of angiogenesis | |
| HK1104961B (en) | Carboline derivatives useful in the inhibition of angiogenesis | |
| HK1167405A (en) | Carboline derivatives useful in the inhibition of angiogenesis |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PSEA | Patent sealed | ||
| RENW | Renewal (renewal fees accepted) | ||
| RENW | Renewal (renewal fees accepted) |
Free format text: PATENT RENEWED FOR 1 YEAR UNTIL 15 MAR 2016 BY CPA GLOBAL Effective date: 20150131 |
|
| RENW | Renewal (renewal fees accepted) |
Free format text: PATENT RENEWED FOR 1 YEAR UNTIL 15 MAR 2017 BY CPA GLOBAL Effective date: 20160129 |
|
| RENW | Renewal (renewal fees accepted) |
Free format text: PATENT RENEWED FOR 1 YEAR UNTIL 15 MAR 2018 BY CPA GLOBAL Effective date: 20170127 |
|
| RENW | Renewal (renewal fees accepted) |
Free format text: PATENT RENEWED FOR 1 YEAR UNTIL 15 MAR 2019 BY JAMES + WELLS Effective date: 20180228 |
|
| RENW | Renewal (renewal fees accepted) |
Free format text: PATENT RENEWED FOR 1 YEAR UNTIL 15 MAR 2020 BY JAMES + WELLS Effective date: 20190307 |
|
| RENW | Renewal (renewal fees accepted) |
Free format text: PATENT RENEWED FOR 1 YEAR UNTIL 15 MAR 2021 BY IPAN GMBH Effective date: 20200214 |
|
| RENW | Renewal (renewal fees accepted) |
Free format text: PATENT RENEWED FOR 1 YEAR UNTIL 15 MAR 2022 BY ANAQUA SERVICES Effective date: 20210217 |
|
| RENW | Renewal (renewal fees accepted) |
Free format text: PATENT RENEWED FOR 1 YEAR UNTIL 15 MAR 2023 BY ANAQUA SERVICES Effective date: 20220218 |
|
| RENW | Renewal (renewal fees accepted) |
Free format text: PATENT RENEWED FOR 1 YEAR UNTIL 15 MAR 2024 BY ANAQUA SERVICES Effective date: 20230222 |
|
| LAPS | Patent lapsed |