AU2007207743B2 - Thiazole compounds as protein kinase B (PKB) inhibitors - Google Patents
Thiazole compounds as protein kinase B (PKB) inhibitors Download PDFInfo
- Publication number
- AU2007207743B2 AU2007207743B2 AU2007207743A AU2007207743A AU2007207743B2 AU 2007207743 B2 AU2007207743 B2 AU 2007207743B2 AU 2007207743 A AU2007207743 A AU 2007207743A AU 2007207743 A AU2007207743 A AU 2007207743A AU 2007207743 B2 AU2007207743 B2 AU 2007207743B2
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- Australia
- Prior art keywords
- amino
- alkyl
- phenyl
- compound
- thiazol
- 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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- 108091008611 Protein Kinase B Proteins 0.000 title description 54
- 239000003112 inhibitor Substances 0.000 title description 13
- 150000003557 thiazoles Chemical class 0.000 title description 5
- 102000005765 Proto-Oncogene Proteins c-akt Human genes 0.000 title description 3
- -1 substituted Chemical class 0.000 claims description 405
- 150000001875 compounds Chemical class 0.000 claims description 300
- 125000003118 aryl group Chemical group 0.000 claims description 172
- 239000000203 mixture Substances 0.000 claims description 144
- 125000000217 alkyl group Chemical group 0.000 claims description 136
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 100
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 99
- 125000001072 heteroaryl group Chemical group 0.000 claims description 95
- 238000000034 method Methods 0.000 claims description 91
- 125000000623 heterocyclic group Chemical group 0.000 claims description 72
- 206010028980 Neoplasm Diseases 0.000 claims description 64
- 102100033810 RAC-alpha serine/threonine-protein kinase Human genes 0.000 claims description 56
- RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical compound NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 claims description 53
- 239000003814 drug Substances 0.000 claims description 51
- 201000011510 cancer Diseases 0.000 claims description 48
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 48
- 201000010099 disease Diseases 0.000 claims description 47
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 42
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 41
- 239000008194 pharmaceutical composition Substances 0.000 claims description 39
- 150000003839 salts Chemical class 0.000 claims description 38
- 230000001404 mediated effect Effects 0.000 claims description 34
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 34
- 125000005842 heteroatom Chemical group 0.000 claims description 33
- 125000004432 carbon atom Chemical group C* 0.000 claims description 32
- 125000005843 halogen group Chemical group 0.000 claims description 32
- 241000124008 Mammalia Species 0.000 claims description 31
- 229910052739 hydrogen Inorganic materials 0.000 claims description 30
- 125000006308 propyl amino group Chemical group 0.000 claims description 29
- 108091000080 Phosphotransferase Proteins 0.000 claims description 27
- 102000020233 phosphotransferase Human genes 0.000 claims description 27
- JYGFTBXVXVMTGB-UHFFFAOYSA-N indolin-2-one Chemical compound C1=CC=C2NC(=O)CC2=C1 JYGFTBXVXVMTGB-UHFFFAOYSA-N 0.000 claims description 26
- 125000004076 pyridyl group Chemical group 0.000 claims description 25
- 125000005605 benzo group Chemical group 0.000 claims description 24
- 125000002619 bicyclic group Chemical group 0.000 claims description 24
- 125000001424 substituent group Chemical group 0.000 claims description 24
- 125000006413 ring segment Chemical group 0.000 claims description 22
- 229940124597 therapeutic agent Drugs 0.000 claims description 22
- 238000002360 preparation method Methods 0.000 claims description 20
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 18
- 125000002950 monocyclic group Chemical group 0.000 claims description 18
- 125000004122 cyclic group Chemical group 0.000 claims description 17
- 229920006395 saturated elastomer Polymers 0.000 claims description 17
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 16
- 125000002837 carbocyclic group Chemical group 0.000 claims description 15
- 229910052799 carbon Inorganic materials 0.000 claims description 15
- 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 claims description 15
- 230000010261 cell growth Effects 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- 230000035755 proliferation Effects 0.000 claims description 14
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 12
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 12
- 230000002159 abnormal effect Effects 0.000 claims description 12
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 12
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 12
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 11
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 11
- 125000001624 naphthyl group Chemical group 0.000 claims description 10
- 125000004496 thiazol-5-yl group Chemical group S1C=NC=C1* 0.000 claims description 10
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 9
- 125000001041 indolyl group Chemical group 0.000 claims description 9
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
- 125000006574 non-aromatic ring group Chemical group 0.000 claims description 9
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 9
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims description 9
- 125000001544 thienyl group Chemical group 0.000 claims description 9
- ASSKVPFEZFQQNQ-UHFFFAOYSA-N 2-benzoxazolinone Chemical compound C1=CC=C2OC(O)=NC2=C1 ASSKVPFEZFQQNQ-UHFFFAOYSA-N 0.000 claims description 8
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 8
- 239000003937 drug carrier Substances 0.000 claims description 8
- 125000002541 furyl group Chemical group 0.000 claims description 8
- 230000005764 inhibitory process Effects 0.000 claims description 8
- YLYDMVVGZJUBDE-UHFFFAOYSA-N 4-(methoxymethyl)-1,3-thiazol-2-amine Chemical compound COCC1=CSC(N)=N1 YLYDMVVGZJUBDE-UHFFFAOYSA-N 0.000 claims description 7
- 101100481408 Danio rerio tie2 gene Proteins 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 125000004495 thiazol-4-yl group Chemical group S1C=NC(=C1)* 0.000 claims description 7
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 6
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 6
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 6
- 102000008130 Cyclic AMP-Dependent Protein Kinases Human genes 0.000 claims description 6
- 101100481410 Mus musculus Tek gene Proteins 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 6
- 102000052116 epidermal growth factor receptor activity proteins Human genes 0.000 claims description 6
- 108700015053 epidermal growth factor receptor activity proteins Proteins 0.000 claims description 6
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 6
- YOHYSYJDKVYCJI-UHFFFAOYSA-N n-[3-[[6-[3-(trifluoromethyl)anilino]pyrimidin-4-yl]amino]phenyl]cyclopropanecarboxamide Chemical compound FC(F)(F)C1=CC=CC(NC=2N=CN=C(NC=3C=C(NC(=O)C4CC4)C=CC=3)C=2)=C1 YOHYSYJDKVYCJI-UHFFFAOYSA-N 0.000 claims description 6
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims description 5
- 102000001267 GSK3 Human genes 0.000 claims description 5
- 108060006662 GSK3 Proteins 0.000 claims description 5
- 101000669921 Homo sapiens Rho-associated protein kinase 2 Proteins 0.000 claims description 5
- 101001001648 Homo sapiens Serine/threonine-protein kinase pim-2 Proteins 0.000 claims description 5
- 108090000723 Insulin-Like Growth Factor I Proteins 0.000 claims description 5
- 102100039314 Rho-associated protein kinase 2 Human genes 0.000 claims description 5
- 102100036120 Serine/threonine-protein kinase pim-2 Human genes 0.000 claims description 5
- 125000004537 indazol-5-yl group Chemical group N1N=CC2=CC(=CC=C12)* 0.000 claims description 5
- VYCKDIRCVDCQAE-UHFFFAOYSA-N isoquinolin-3-amine Chemical compound C1=CC=C2C=NC(N)=CC2=C1 VYCKDIRCVDCQAE-UHFFFAOYSA-N 0.000 claims description 5
- NFVJNJQRWPQVOA-UHFFFAOYSA-N n-[2-chloro-5-(trifluoromethyl)phenyl]-2-[3-(4-ethyl-5-ethylsulfanyl-1,2,4-triazol-3-yl)piperidin-1-yl]acetamide Chemical compound CCN1C(SCC)=NN=C1C1CN(CC(=O)NC=2C(=CC=C(C=2)C(F)(F)F)Cl)CCC1 NFVJNJQRWPQVOA-UHFFFAOYSA-N 0.000 claims description 5
- OTYWCJLDOQPLSL-KRWDZBQOSA-N (2s)-1-n-[4-(methoxymethyl)-5-(1,6-naphthyridin-2-yl)-1,3-thiazol-2-yl]-3-[4-(trifluoromethyl)phenyl]propane-1,2-diamine Chemical compound C([C@H](N)CNC1=NC(=C(S1)C=1N=C2C=CN=CC2=CC=1)COC)C1=CC=C(C(F)(F)F)C=C1 OTYWCJLDOQPLSL-KRWDZBQOSA-N 0.000 claims description 4
- VGPQUILKMXOHDS-IBGZPJMESA-N (2s)-3-(3-chlorophenyl)-1-n-(5-isoquinolin-6-yl-1,3-thiazol-2-yl)propane-1,2-diamine Chemical compound C([C@@H](CNC=1SC(=CN=1)C=1C=C2C=CN=CC2=CC=1)N)C1=CC=CC(Cl)=C1 VGPQUILKMXOHDS-IBGZPJMESA-N 0.000 claims description 4
- PNAFRZGWUVQUKH-UHFFFAOYSA-N 1,3-thiazole-4-carbonitrile Chemical compound N#CC1=CSC=N1 PNAFRZGWUVQUKH-UHFFFAOYSA-N 0.000 claims description 4
- HYAHAIVZFRFEBU-UHFFFAOYSA-N 4-[4-(trifluoromethyl)phenyl]-1,3-thiazol-2-amine Chemical compound S1C(N)=NC(C=2C=CC(=CC=2)C(F)(F)F)=C1 HYAHAIVZFRFEBU-UHFFFAOYSA-N 0.000 claims description 4
- 102100035427 Forkhead box protein O1 Human genes 0.000 claims description 4
- 101000877727 Homo sapiens Forkhead box protein O1 Proteins 0.000 claims description 4
- 108010001127 Insulin Receptor Proteins 0.000 claims description 4
- 102000003923 Protein Kinase C Human genes 0.000 claims description 4
- 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 claims description 4
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 claims description 4
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 4
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims description 4
- 125000002971 oxazolyl group Chemical group 0.000 claims description 4
- 125000004043 oxo group Chemical group O=* 0.000 claims description 4
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 4
- TYCJPDLIEVIZMC-INIZCTEOSA-N (2s)-1-n-[5-(3-methyl-2h-indazol-5-yl)-1,3-thiazol-2-yl]-3-phenylpropane-1,2-diamine Chemical compound C([C@H](N)CNC1=NC=C(S1)C1=CC=C2NN=C(C2=C1)C)C1=CC=CC=C1 TYCJPDLIEVIZMC-INIZCTEOSA-N 0.000 claims description 3
- BLAVYYFRUYHSSA-IBGZPJMESA-N (2s)-3-(1h-indol-3-yl)-1-n-(5-isoquinolin-6-yl-1,3-thiazol-2-yl)propane-1,2-diamine Chemical compound C1=CC=C2C(C[C@@H](CNC=3SC(=CN=3)C=3C=C4C=CN=CC4=CC=3)N)=CNC2=C1 BLAVYYFRUYHSSA-IBGZPJMESA-N 0.000 claims description 3
- LJVIDZQPGQAVHM-INIZCTEOSA-N (2s)-3-(4-chlorophenyl)-1-n-[5-(1h-indazol-5-yl)-1,3-thiazol-2-yl]propane-1,2-diamine Chemical compound C([C@@H](CNC=1SC(=CN=1)C=1C=C2C=NNC2=CC=1)N)C1=CC=C(Cl)C=C1 LJVIDZQPGQAVHM-INIZCTEOSA-N 0.000 claims description 3
- YDTDKKULPWTHRV-UHFFFAOYSA-N 1H-indazol-3-amine Chemical compound C1=CC=C2C(N)=NNC2=C1 YDTDKKULPWTHRV-UHFFFAOYSA-N 0.000 claims description 3
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims description 3
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 3
- 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 claims description 3
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 3
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000004863 4-trifluoromethoxyphenyl group Chemical group [H]C1=C([H])C(OC(F)(F)F)=C([H])C([H])=C1* 0.000 claims description 3
- WMFQVXIDVPQEPP-VYIIXAMBSA-N 5-[2-[[(2s)-2-amino-3-phenylpropyl]amino]-1,3-thiazol-5-yl]-3-methyl-1,3-dihydroindol-2-one Chemical compound C([C@H](N)CNC1=NC=C(S1)C1=CC=C2NC(=O)C(C2=C1)C)C1=CC=CC=C1 WMFQVXIDVPQEPP-VYIIXAMBSA-N 0.000 claims description 3
- 101100456282 Caenorhabditis elegans mcm-4 gene Proteins 0.000 claims description 3
- 108010053099 Vascular Endothelial Growth Factor Receptor-2 Proteins 0.000 claims description 3
- QDYCTALEGOKETB-IBGZPJMESA-N [2-[[(2s)-2-amino-3-[4-(trifluoromethyl)phenyl]propyl]amino]-5-isoquinolin-6-yl-1,3-thiazol-4-yl]methanol Chemical compound C([C@@H](CNC=1SC(=C(CO)N=1)C=1C=C2C=CN=CC2=CC=1)N)C1=CC=C(C(F)(F)F)C=C1 QDYCTALEGOKETB-IBGZPJMESA-N 0.000 claims description 3
- 125000005036 alkoxyphenyl group Chemical group 0.000 claims description 3
- 125000000068 chlorophenyl group Chemical group 0.000 claims description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims description 3
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 claims description 3
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 3
- RREBSXDCHJHRDT-FXMQYSIJSA-N (2s)-1-n-[5-isoquinolin-6-yl-4-(1-methoxyethyl)-1,3-thiazol-2-yl]-3-[4-(trifluoromethyl)phenyl]propane-1,2-diamine Chemical compound C([C@H](N)CNC1=NC(=C(S1)C=1C=C2C=CN=CC2=CC=1)C(C)OC)C1=CC=C(C(F)(F)F)C=C1 RREBSXDCHJHRDT-FXMQYSIJSA-N 0.000 claims description 2
- WNUCYWQQQOPMBN-INIZCTEOSA-N 5-[2-[[(2s)-2-amino-3-(4-chlorophenyl)propyl]amino]-1,3-thiazol-5-yl]-1,3-dihydroindol-2-one Chemical compound C([C@@H](CNC=1SC(=CN=1)C=1C=C2CC(=O)NC2=CC=1)N)C1=CC=C(Cl)C=C1 WNUCYWQQQOPMBN-INIZCTEOSA-N 0.000 claims description 2
- HBAJEILBHKIJBU-AWEZNQCLSA-N 6-[2-[[(2s)-2-amino-3-(4-chlorophenyl)propyl]amino]-1,3-thiazol-5-yl]-3h-1,3-benzoxazol-2-one Chemical compound C([C@@H](CNC=1SC(=CN=1)C=1C=C2OC(=O)NC2=CC=1)N)C1=CC=C(Cl)C=C1 HBAJEILBHKIJBU-AWEZNQCLSA-N 0.000 claims description 2
- FNQWGQWNXGGAFV-AWEZNQCLSA-N 6-[2-[[(2s)-2-amino-3-(4-methoxyphenyl)propyl]amino]-1,3-thiazol-5-yl]-3h-1,3-benzoxazol-2-one Chemical compound C1=CC(OC)=CC=C1C[C@H](N)CNC1=NC=C(C=2C=C3OC(=O)NC3=CC=2)S1 FNQWGQWNXGGAFV-AWEZNQCLSA-N 0.000 claims description 2
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- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 2
- IJAPPYDYQCXOEF-UHFFFAOYSA-N phthalazin-1(2H)-one Chemical compound C1=CC=C2C(=O)NN=CC2=C1 IJAPPYDYQCXOEF-UHFFFAOYSA-N 0.000 claims description 2
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- 125000004212 difluorophenyl group Chemical group 0.000 claims 2
- LVKPDCDJLJWKLG-FQEVSTJZSA-N (2s)-1-n-[5-isoquinolin-6-yl-4-(methylaminomethyl)-1,3-thiazol-2-yl]-3-[4-(trifluoromethyl)phenyl]propane-1,2-diamine Chemical compound C([C@H](N)CNC1=NC(=C(S1)C=1C=C2C=CN=CC2=CC=1)CNC)C1=CC=C(C(F)(F)F)C=C1 LVKPDCDJLJWKLG-FQEVSTJZSA-N 0.000 claims 1
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Classifications
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
- A61K31/427—Thiazoles not condensed and containing further heterocyclic rings
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- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
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- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
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- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
Landscapes
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
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| PCT/US2007/000871 WO2007084391A2 (en) | 2006-01-18 | 2007-01-11 | Thiazole compounds as protein kinase b ( pkb) inhibitors |
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| CN101702905A (zh) | 2007-02-13 | 2010-05-05 | 先灵公司 | 功能选择性α2C肾上腺素能受体激动剂 |
| AU2008276521B2 (en) | 2007-07-17 | 2011-11-03 | Amgen Inc. | Heterocyclic modulators of PKB |
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| US20110092423A1 (en) * | 2008-06-26 | 2011-04-21 | GlaxoSmithKline, LLC | INHIBITORS OF Akt ACTIVITY |
| US9643922B2 (en) | 2008-08-18 | 2017-05-09 | Yale University | MIF modulators |
| US9540322B2 (en) | 2008-08-18 | 2017-01-10 | Yale University | MIF modulators |
| BRPI0917394A2 (pt) * | 2008-08-18 | 2019-09-24 | Univ Yale | moduladores de mif |
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| CN111603466B (zh) * | 2020-06-29 | 2022-07-22 | 江南大学 | 一种乙酮类化合物在制备治疗肿瘤药物中的应用 |
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| CN116813608B (zh) * | 2023-06-08 | 2024-03-22 | 英矽智能科技(上海)有限公司 | 噻唑类化合物及其应用 |
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| TW200738657A (en) | 2007-10-16 |
| IL192751A0 (en) | 2009-02-11 |
| US7514566B2 (en) | 2009-04-07 |
| US20070173506A1 (en) | 2007-07-26 |
| UY30098A1 (es) | 2007-10-31 |
| WO2007084391A3 (en) | 2008-03-20 |
| EP1981884B1 (en) | 2012-06-13 |
| JP5199885B2 (ja) | 2013-05-15 |
| US8084479B2 (en) | 2011-12-27 |
| CA2636077C (en) | 2012-01-03 |
| BRPI0706621A2 (pt) | 2011-04-05 |
| ES2389062T3 (es) | 2012-10-22 |
| CA2636077A1 (en) | 2007-07-26 |
| WO2007084391A2 (en) | 2007-07-26 |
| PE20071114A1 (es) | 2008-01-10 |
| UA91895C2 (en) | 2010-09-10 |
| US20090270445A1 (en) | 2009-10-29 |
| AU2007207743A1 (en) | 2007-07-26 |
| CN101421265A (zh) | 2009-04-29 |
| MY149143A (en) | 2013-07-15 |
| EP1981884A2 (en) | 2008-10-22 |
| NO20083572L (no) | 2008-10-17 |
| KR20080091369A (ko) | 2008-10-10 |
| AR059064A1 (es) | 2008-03-12 |
| JP2009525960A (ja) | 2009-07-16 |
| CR10211A (es) | 2008-10-03 |
| ZA200806386B (en) | 2009-11-25 |
| EA200801716A1 (ru) | 2009-04-28 |
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