JP2006512357A - Ｐｉ３ｋの阻害剤としてのベンゾキサジンおよびその誘導体 - Google Patents
Ｐｉ３ｋの阻害剤としてのベンゾキサジンおよびその誘導体 Download PDFInfo
- Publication number
- JP2006512357A JP2006512357A JP2004561828A JP2004561828A JP2006512357A JP 2006512357 A JP2006512357 A JP 2006512357A JP 2004561828 A JP2004561828 A JP 2004561828A JP 2004561828 A JP2004561828 A JP 2004561828A JP 2006512357 A JP2006512357 A JP 2006512357A
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- thioxo
- dihydro
- phenyl
- thiazolidin
- 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.)
- Abandoned
Links
- 108091007960 PI3Ks Proteins 0.000 title claims description 54
- 102000010400 1-phosphatidylinositol-3-kinase activity proteins Human genes 0.000 title claims 3
- 239000003112 inhibitor Substances 0.000 title description 14
- CMLFRMDBDNHMRA-UHFFFAOYSA-N 2h-1,2-benzoxazine Chemical compound C1=CC=C2C=CNOC2=C1 CMLFRMDBDNHMRA-UHFFFAOYSA-N 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 156
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 39
- 150000003839 salts Chemical class 0.000 claims abstract description 28
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 20
- 208000027866 inflammatory disease Diseases 0.000 claims abstract description 7
- 229910052727 yttrium Inorganic materials 0.000 claims abstract description 3
- -1 4-pyridinyl Chemical group 0.000 claims description 154
- 125000000217 alkyl group Chemical group 0.000 claims description 38
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 37
- 208000035475 disorder Diseases 0.000 claims description 24
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 23
- 229910052739 hydrogen Inorganic materials 0.000 claims description 21
- 230000001404 mediated effect Effects 0.000 claims description 21
- 229910052799 carbon Inorganic materials 0.000 claims description 19
- 125000003342 alkenyl group Chemical group 0.000 claims description 16
- 125000000304 alkynyl group Chemical group 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 16
- 125000001624 naphthyl group Chemical group 0.000 claims description 15
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 13
- 239000005977 Ethylene Substances 0.000 claims description 13
- 125000006545 (C1-C9) alkyl group Chemical group 0.000 claims description 10
- 239000003937 drug carrier Substances 0.000 claims description 9
- 125000001072 heteroaryl group Chemical group 0.000 claims description 9
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 4
- 125000006580 bicyclic heterocycloalkyl group Chemical group 0.000 claims description 4
- 201000008482 osteoarthritis Diseases 0.000 claims description 4
- ADHBQTVRFHHGSD-UHFFFAOYSA-N phenyl 6-[(4-oxo-2-sulfanylidene-1,3-thiazolidin-5-ylidene)methyl]-2,3-dihydro-1,4-benzoxazine-4-carboxylate Chemical compound C1COC2=CC=C(C=C3C(NC(=S)S3)=O)C=C2N1C(=O)OC1=CC=CC=C1 ADHBQTVRFHHGSD-UHFFFAOYSA-N 0.000 claims description 4
- 125000003386 piperidinyl group Chemical group 0.000 claims description 4
- AZHNJGMAHPCYTO-UHFFFAOYSA-N (4-methoxycarbonylphenyl) 6-[(4-oxo-2-sulfanylidene-1,3-thiazolidin-5-ylidene)methyl]-2,3-dihydro-1,4-benzoxazine-4-carboxylate Chemical compound C1=CC(C(=O)OC)=CC=C1OC(=O)N1C2=CC(C=C3C(NC(=S)S3)=O)=CC=C2OCC1 AZHNJGMAHPCYTO-UHFFFAOYSA-N 0.000 claims description 3
- SZJWGDUDJSGXGD-UHFFFAOYSA-N (4-methylphenyl) 6-[(4-oxo-2-sulfanylidene-1,3-thiazolidin-5-ylidene)methyl]-2,3-dihydro-1,4-benzoxazine-4-carboxylate Chemical compound C1=CC(C)=CC=C1OC(=O)N1C2=CC(C=C3C(NC(=S)S3)=O)=CC=C2OCC1 SZJWGDUDJSGXGD-UHFFFAOYSA-N 0.000 claims description 3
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 3
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 3
- SCBNEBCVYMOMFL-UHFFFAOYSA-N 5-[(4-heptanoyl-2,3-dihydro-1,4-benzoxazin-6-yl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one Chemical compound C1=C2N(C(=O)CCCCCC)CCOC2=CC=C1C=C1SC(=S)NC1=O SCBNEBCVYMOMFL-UHFFFAOYSA-N 0.000 claims description 3
- PKHANDDFNUXAFV-UHFFFAOYSA-N 5-[(4-pentanoyl-2,3-dihydro-1,4-benzoxazin-6-yl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one Chemical compound C1=C2N(C(=O)CCCC)CCOC2=CC=C1C=C1SC(=S)NC1=O PKHANDDFNUXAFV-UHFFFAOYSA-N 0.000 claims description 3
- UWKBMECNTWQSLY-UHFFFAOYSA-N 5-[[4-(2-methylpropanoyl)-2,3-dihydro-1,4-benzoxazin-6-yl]methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one Chemical compound C1=C2N(C(=O)C(C)C)CCOC2=CC=C1C=C1SC(=S)NC1=O UWKBMECNTWQSLY-UHFFFAOYSA-N 0.000 claims description 3
- WFJYMLNJPHSLNA-UHFFFAOYSA-N 5-[[4-(2-phenylmethoxyacetyl)-2,3-dihydro-1,4-benzoxazin-6-yl]methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one Chemical compound C1COC2=CC=C(C=C3C(NC(=S)S3)=O)C=C2N1C(=O)COCC1=CC=CC=C1 WFJYMLNJPHSLNA-UHFFFAOYSA-N 0.000 claims description 3
- LYJCNRVAIPWBKM-UHFFFAOYSA-N 5-[[4-(2-phenylsulfanylacetyl)-2,3-dihydro-1,4-benzoxazin-6-yl]methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one Chemical compound C1COC2=CC=C(C=C3C(NC(=S)S3)=O)C=C2N1C(=O)CSC1=CC=CC=C1 LYJCNRVAIPWBKM-UHFFFAOYSA-N 0.000 claims description 3
- GMMCWLUTYRNKNT-UHFFFAOYSA-N 5-[[4-(3-cyclopentylpropanoyl)-2,3-dihydro-1,4-benzoxazin-6-yl]methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one Chemical compound C1COC2=CC=C(C=C3C(NC(=S)S3)=O)C=C2N1C(=O)CCC1CCCC1 GMMCWLUTYRNKNT-UHFFFAOYSA-N 0.000 claims description 3
- UBDWHOTZVUMAGD-UHFFFAOYSA-N 5-[[4-(3-phenylprop-2-enoyl)-2,3-dihydro-1,4-benzoxazin-6-yl]methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one Chemical compound C1COC2=CC=C(C=C3C(NC(=S)S3)=O)C=C2N1C(=O)C=CC1=CC=CC=C1 UBDWHOTZVUMAGD-UHFFFAOYSA-N 0.000 claims description 3
- ABMAEMXZZIQZAW-UHFFFAOYSA-N 6-[(4-oxo-2-sulfanylidene-1,3-thiazolidin-5-ylidene)methyl]-n-(2-phenylethyl)-2,3-dihydro-1,4-benzoxazine-4-carboxamide Chemical compound C1COC2=CC=C(C=C3C(NC(=S)S3)=O)C=C2N1C(=O)NCCC1=CC=CC=C1 ABMAEMXZZIQZAW-UHFFFAOYSA-N 0.000 claims description 3
- BOJXKPUZPWUBKG-UHFFFAOYSA-N 6-[(4-oxo-2-sulfanylidene-1,3-thiazolidin-5-ylidene)methyl]-n-[3-(trifluoromethyl)phenyl]-2,3-dihydro-1,4-benzoxazine-4-carboxamide Chemical compound FC(F)(F)C1=CC=CC(NC(=O)N2C3=CC(C=C4C(NC(=S)S4)=O)=CC=C3OCC2)=C1 BOJXKPUZPWUBKG-UHFFFAOYSA-N 0.000 claims description 3
- 206010002556 Ankylosing Spondylitis Diseases 0.000 claims description 3
- 208000023275 Autoimmune disease Diseases 0.000 claims description 3
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 3
- 125000004601 benzofurazanyl group Chemical group N1=C2C(=NO1)C(=CC=C2)* 0.000 claims description 3
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 3
- YMPZGWKUVRLVKJ-UHFFFAOYSA-N methyl 8-oxo-8-[6-[(4-oxo-2-sulfanylidene-1,3-thiazolidin-5-ylidene)methyl]-2,3-dihydro-1,4-benzoxazin-4-yl]octanoate Chemical compound C1=C2N(C(=O)CCCCCCC(=O)OC)CCOC2=CC=C1C=C1SC(=S)NC1=O YMPZGWKUVRLVKJ-UHFFFAOYSA-N 0.000 claims description 3
- GSMHWGJGKAOCFZ-UHFFFAOYSA-N n-(3-chlorophenyl)-6-[(4-oxo-2-sulfanylidene-1,3-thiazolidin-5-ylidene)methyl]-2,3-dihydro-1,4-benzoxazine-4-carboxamide Chemical compound ClC1=CC=CC(NC(=O)N2C3=CC(C=C4C(NC(=S)S4)=O)=CC=C3OCC2)=C1 GSMHWGJGKAOCFZ-UHFFFAOYSA-N 0.000 claims description 3
- OMCSAMOTVJTYBH-UHFFFAOYSA-N n-(4-chlorophenyl)-6-[(4-oxo-2-sulfanylidene-1,3-thiazolidin-5-ylidene)methyl]-2,3-dihydro-1,4-benzoxazine-4-carboxamide Chemical compound C1=CC(Cl)=CC=C1NC(=O)N1C2=CC(C=C3C(NC(=S)S3)=O)=CC=C2OCC1 OMCSAMOTVJTYBH-UHFFFAOYSA-N 0.000 claims description 3
- KNTWQLFICXLUMJ-UHFFFAOYSA-N n-cyclopentyl-6-[(4-oxo-2-sulfanylidene-1,3-thiazolidin-5-ylidene)methyl]-2,3-dihydro-1,4-benzoxazine-4-carboxamide Chemical compound C1COC2=CC=C(C=C3C(NC(=S)S3)=O)C=C2N1C(=O)NC1CCCC1 KNTWQLFICXLUMJ-UHFFFAOYSA-N 0.000 claims description 3
- XSDJJZZCSAQENW-UHFFFAOYSA-N naphthalen-1-yl 6-[(4-oxo-2-sulfanylidene-1,3-thiazolidin-5-ylidene)methyl]-2,3-dihydro-1,4-benzoxazine-4-carboxylate Chemical compound C=1C=CC2=CC=CC=C2C=1OC(=O)N(C1=C2)CCOC1=CC=C2C=C1SC(=S)NC1=O XSDJJZZCSAQENW-UHFFFAOYSA-N 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 3
- 125000001544 thienyl group Chemical group 0.000 claims description 3
- KPCZJLGGXRGYIE-UHFFFAOYSA-N [C]1=CC=CN=C1 Chemical group [C]1=CC=CN=C1 KPCZJLGGXRGYIE-UHFFFAOYSA-N 0.000 claims description 2
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 2
- NPGBBBUQVSTPBS-UHFFFAOYSA-N n-(3,4-dichlorophenyl)-6-[(4-oxo-2-sulfanylidene-1,3-thiazolidin-5-ylidene)methyl]-2,3-dihydro-1,4-benzoxazine-4-carboxamide Chemical compound C1=C(Cl)C(Cl)=CC=C1NC(=O)N1C2=CC(C=C3C(NC(=S)S3)=O)=CC=C2OCC1 NPGBBBUQVSTPBS-UHFFFAOYSA-N 0.000 claims description 2
- BSTXURKZHUFJNL-UHFFFAOYSA-N n-(3,5-dimethylphenyl)-6-[(4-oxo-2-sulfanylidene-1,3-thiazolidin-5-ylidene)methyl]-2,3-dihydro-1,4-benzoxazine-4-carboxamide Chemical compound CC1=CC(C)=CC(NC(=O)N2C3=CC(C=C4C(NC(=S)S4)=O)=CC=C3OCC2)=C1 BSTXURKZHUFJNL-UHFFFAOYSA-N 0.000 claims description 2
- 201000010099 disease Diseases 0.000 abstract description 15
- 208000024172 Cardiovascular disease Diseases 0.000 abstract description 4
- 239000000126 substance Substances 0.000 abstract description 3
- 201000011529 cardiovascular cancer Diseases 0.000 abstract description 2
- 229910052700 potassium Inorganic materials 0.000 abstract description 2
- 239000000543 intermediate Substances 0.000 description 54
- 102000038030 PI3Ks Human genes 0.000 description 51
- 108090000430 Phosphatidylinositol 3-kinases Proteins 0.000 description 50
- 239000000203 mixture Substances 0.000 description 39
- 239000011541 reaction mixture Substances 0.000 description 37
- 239000000047 product Substances 0.000 description 32
- 238000004452 microanalysis Methods 0.000 description 31
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
- 239000000243 solution Substances 0.000 description 27
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 25
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 24
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 20
- 125000004432 carbon atom Chemical group C* 0.000 description 19
- 238000006243 chemical reaction Methods 0.000 description 18
- 125000000753 cycloalkyl group Chemical group 0.000 description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 15
- 239000002253 acid Substances 0.000 description 15
- 210000004027 cell Anatomy 0.000 description 15
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 14
- 238000002360 preparation method Methods 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- 238000012360 testing method Methods 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
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- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 12
- 150000002632 lipids Chemical class 0.000 description 12
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 12
- 235000019341 magnesium sulphate Nutrition 0.000 description 12
- 230000002829 reductive effect Effects 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
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- 108091006027 G proteins Proteins 0.000 description 10
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- 125000002252 acyl group Chemical group 0.000 description 10
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- 125000002950 monocyclic group Chemical group 0.000 description 10
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- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 10
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- 125000003118 aryl group Chemical group 0.000 description 9
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 239000011347 resin Substances 0.000 description 9
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- 101710189301 101 kDa malaria antigen Proteins 0.000 description 8
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- 241000701447 unidentified baculovirus Species 0.000 description 8
- 125000003341 7 membered heterocyclic group Chemical group 0.000 description 7
- 150000001412 amines Chemical class 0.000 description 7
- 125000005343 heterocyclic alkyl group Chemical group 0.000 description 7
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- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 description 5
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- NRHMKIHPTBHXPF-TUJRSCDTSA-M sodium cholate Chemical compound [Na+].C([C@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC([O-])=O)C)[C@@]2(C)[C@@H](O)C1 NRHMKIHPTBHXPF-TUJRSCDTSA-M 0.000 description 5
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- GDBQQVLCIARPGH-UHFFFAOYSA-N Leupeptin Natural products CC(C)CC(NC(C)=O)C(=O)NC(CC(C)C)C(=O)NC(C=O)CCCN=C(N)N GDBQQVLCIARPGH-UHFFFAOYSA-N 0.000 description 4
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- 238000004458 analytical method Methods 0.000 description 4
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- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 4
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- VGKDLMBJGBXTGI-SJCJKPOMSA-N sertraline Chemical compound C1([C@@H]2CC[C@@H](C3=CC=CC=C32)NC)=CC=C(Cl)C(Cl)=C1 VGKDLMBJGBXTGI-SJCJKPOMSA-N 0.000 description 1
- 229960002073 sertraline Drugs 0.000 description 1
- 230000019491 signal transduction Effects 0.000 description 1
- XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
- 229960002855 simvastatin Drugs 0.000 description 1
- QFJCIRLUMZQUOT-HPLJOQBZSA-N sirolimus Chemical compound C1C[C@@H](O)[C@H](OC)C[C@@H]1C[C@@H](C)[C@H]1OC(=O)[C@@H]2CCCCN2C(=O)C(=O)[C@](O)(O2)[C@H](C)CC[C@H]2C[C@H](OC)/C(C)=C/C=C/C=C/[C@@H](C)C[C@@H](C)C(=O)[C@H](OC)[C@H](O)/C(C)=C/[C@@H](C)C(=O)C1 QFJCIRLUMZQUOT-HPLJOQBZSA-N 0.000 description 1
- 229960002930 sirolimus Drugs 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 1
- YWIVKILSMZOHHF-QJZPQSOGSA-N sodium;(2s,3s,4s,5r,6r)-6-[(2s,3r,4r,5s,6r)-3-acetamido-2-[(2s,3s,4r,5r,6r)-6-[(2r,3r,4r,5s,6r)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-carboxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3,4,5-trihydroxyoxane-2- Chemical compound [Na+].CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@H](O3)C(O)=O)O)[C@H](O)[C@@H](CO)O2)NC(C)=O)[C@@H](C(O)=O)O1 YWIVKILSMZOHHF-QJZPQSOGSA-N 0.000 description 1
- 239000007909 solid dosage form Substances 0.000 description 1
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- 235000019698 starch Nutrition 0.000 description 1
- 229960005202 streptokinase Drugs 0.000 description 1
- TYFQFVWCELRYAO-UHFFFAOYSA-L suberate(2-) Chemical compound [O-]C(=O)CCCCCCC([O-])=O TYFQFVWCELRYAO-UHFFFAOYSA-L 0.000 description 1
- 125000005415 substituted alkoxy group Chemical group 0.000 description 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
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- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- YLJREFDVOIBQDA-UHFFFAOYSA-N tacrine Chemical compound C1=CC=C2C(N)=C(CCCC3)C3=NC2=C1 YLJREFDVOIBQDA-UHFFFAOYSA-N 0.000 description 1
- 229960001685 tacrine Drugs 0.000 description 1
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- DKPFODGZWDEEBT-QFIAKTPHSA-N taxane Chemical class C([C@]1(C)CCC[C@@H](C)[C@H]1C1)C[C@H]2[C@H](C)CC[C@@H]1C2(C)C DKPFODGZWDEEBT-QFIAKTPHSA-N 0.000 description 1
- 229940063683 taxotere Drugs 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 125000005958 tetrahydrothienyl group Chemical group 0.000 description 1
- 125000004632 tetrahydrothiopyranyl group Chemical group S1C(CCCC1)* 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 230000004797 therapeutic response Effects 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 150000001467 thiazolidinediones Chemical class 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001583 thiepanyl group Chemical group 0.000 description 1
- 125000002053 thietanyl group Chemical group 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
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- 201000002510 thyroid cancer Diseases 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
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- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- MIQPIUSUKVNLNT-UHFFFAOYSA-N tolcapone Chemical compound C1=CC(C)=CC=C1C(=O)C1=CC(O)=C(O)C([N+]([O-])=O)=C1 MIQPIUSUKVNLNT-UHFFFAOYSA-N 0.000 description 1
- 229940044693 topoisomerase inhibitor Drugs 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 230000001131 transforming effect Effects 0.000 description 1
- 238000002054 transplantation Methods 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- NFACJZMKEDPNKN-UHFFFAOYSA-N trichlorfon Chemical compound COP(=O)(OC)C(O)C(Cl)(Cl)Cl NFACJZMKEDPNKN-UHFFFAOYSA-N 0.000 description 1
- 125000005455 trithianyl group Chemical group 0.000 description 1
- 229940046728 tumor necrosis factor alpha inhibitor Drugs 0.000 description 1
- 239000002452 tumor necrosis factor alpha inhibitor Substances 0.000 description 1
- 102000003298 tumor necrosis factor receptor Human genes 0.000 description 1
- 229960005356 urokinase Drugs 0.000 description 1
- 239000002525 vasculotropin inhibitor Substances 0.000 description 1
- 229960003048 vinblastine Drugs 0.000 description 1
- JXLYSJRDGCGARV-XQKSVPLYSA-N vincaleukoblastine Chemical compound C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 JXLYSJRDGCGARV-XQKSVPLYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229960002555 zidovudine Drugs 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
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Classifications
-
- 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
- C07D417/02—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
- C07D417/06—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 linked by a carbon chain containing only aliphatic carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- 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
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
-
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Immunology (AREA)
- Rheumatology (AREA)
- Physical Education & Sports Medicine (AREA)
- Pain & Pain Management (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US43522702P | 2002-12-20 | 2002-12-20 | |
| PCT/IB2003/005887 WO2004056820A1 (en) | 2002-12-20 | 2003-12-10 | Benzoxazines and derivatives thereof as inhibitors of pi3ks |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2006512357A true JP2006512357A (ja) | 2006-04-13 |
| JP2006512357A5 JP2006512357A5 (https=) | 2007-02-01 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
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| JP2004561828A Abandoned JP2006512357A (ja) | 2002-12-20 | 2003-12-10 | Ｐｉ３ｋの阻害剤としてのベンゾキサジンおよびその誘導体 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US20040138199A1 (https=) |
| EP (1) | EP1581529A1 (https=) |
| JP (1) | JP2006512357A (https=) |
| AU (1) | AU2003303231A1 (https=) |
| BR (1) | BR0317572A (https=) |
| CA (1) | CA2510851A1 (https=) |
| MX (1) | MXPA05006742A (https=) |
| WO (1) | WO2004056820A1 (https=) |
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| JP2012528165A (ja) * | 2009-05-26 | 2012-11-12 | エクセリクシス， インク． | ＰＩ３Ｋ／ｍＴＯＲの阻害剤としてのベンゾキサゼピンならびにそれらの使用および製造方法 |
| JP2013510825A (ja) * | 2009-11-13 | 2013-03-28 | メルク セローノ ソシエテ アノニム | 三環式ピラゾールアミン誘導体 |
| JP2015506344A (ja) * | 2011-12-22 | 2015-03-02 | ノバルティス アーゲー | ジヒドロ−ベンゾ−オキサジンおよびジヒドロ−ピリド−オキサジン誘導体 |
| JP2017514855A (ja) * | 2014-05-05 | 2017-06-08 | リセラ・コーポレイションＬｙｃｅｒａ Ｃｏｒｐｏｒａｔｉｏｎ | ＲＯＲγアゴニストとして用いるテトラヒドロキノリンスルホンアミド及び関連化合物ならびに疾患の治療 |
| JP2017522300A (ja) * | 2014-06-30 | 2017-08-10 | アストラゼネカ・アクチエボラーグＡｓｔｒａｚｅｎｅｃａ Ａｋｔｉｅｂｏｌａｇ | 鉱質コルチコイド受容体修飾因子としてのベンゾオキサジノンアミド |
| US10421751B2 (en) | 2015-05-05 | 2019-09-24 | Lycera Corporation | Dihydro-2H-benzo[b][1,4]oxazine sulfonamide and related compounds for use as agonists of RORγ and the treatment of disease |
| US10532088B2 (en) | 2014-02-27 | 2020-01-14 | Lycera Corporation | Adoptive cellular therapy using an agonist of retinoic acid receptor-related orphan receptor gamma and related therapeutic methods |
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| US6667300B2 (en) | 2000-04-25 | 2003-12-23 | Icos Corporation | Inhibitors of human phosphatidylinositol 3-kinase delta |
| NZ544784A (en) * | 2003-07-28 | 2009-11-27 | Reddys Lab Inc Dr | Treatment and prevention of cardiovascular events using a beta-adrenergic receptor antagonist, a diuretic, an inhibitor of HMG CoA reductase, an inhibitor of the rennin-angiotensin system and asprin; wherein acidic and basic components are separated. |
| WO2005016348A1 (en) * | 2003-08-14 | 2005-02-24 | Icos Corporation | Method of inhibiting immune responses stimulated by an endogenous factor |
| US7914831B2 (en) | 2004-02-27 | 2011-03-29 | Metaproteomics, Llc | Synergistic anti-inflammatory pharmaceutical compositions and related methods using curcuminoids or methylxanthines |
| SI2612862T1 (sl) | 2004-05-13 | 2017-04-26 | Icos Corporation | Kinazolini kot inhibitorji humane fosfatidilinozitol 3-kinaze delta |
| CA2730540A1 (en) * | 2004-05-13 | 2005-12-01 | Vanderbilt University | Phosphoinositide 3-kinase delta selective inhibitors for inhibiting angiogenesis |
| CA2576765C (en) | 2004-09-03 | 2013-05-28 | Applied Research Systems Ars Holding N.V. | Pyridine methylene azolidinones and use thereof phosphoinositide inhibitors |
| KR20070064660A (ko) | 2004-10-07 | 2007-06-21 | 베링거 인겔하임 인터내셔날 게엠베하 | Ｐｉ３ 키나제 |
| WO2006089106A2 (en) * | 2005-02-17 | 2006-08-24 | Icos Corporation | Phosphoinositide 3-kinase inhibitors for inhibiting leukocyte accumulation |
| CA2618613A1 (en) * | 2005-08-09 | 2007-02-22 | Metaproteomics, Llc | Protein kinase modulation by hops and acacia products |
| AU2006283846B2 (en) | 2005-08-26 | 2012-04-05 | Merck Serono Sa | Pyrazine derivatives and use as PI3K inhibitors |
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| US20070116756A1 (en) * | 2005-11-23 | 2007-05-24 | Dr. Reddy's Laboratories Limited | Stable pharmaceutical compositions |
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| EA201270184A1 (ru) | 2009-07-21 | 2012-08-30 | ГИЛИЭД КАЛИСТОГА ЭлЭлСи | Лечение расстройств печени ингибиторами pi3k |
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| US6355664B1 (en) * | 1997-03-03 | 2002-03-12 | Boehringer Ingelheim Pharmaceuticals, Inc. | Phenylpyrrolidines, phenylimidazolidines, 3-phenyl-1,3-oxizolidines and 3-phenyl-1,3-thiazolidines and their use in the treatment of inflammatory disease |
| ES2788383T3 (es) * | 2000-04-25 | 2020-10-21 | Icos Corp | Inhibidores de delta fosfatidilo-inositol 3-quinasa humana |
| CN1186324C (zh) * | 2000-04-27 | 2005-01-26 | 山之内制药株式会社 | 稠合杂芳基衍生物 |
| US20040092561A1 (en) * | 2002-11-07 | 2004-05-13 | Thomas Ruckle | Azolidinone-vinyl fused -benzene derivatives |
| CN1681811B (zh) * | 2002-07-10 | 2010-05-26 | 默克雪兰诺有限公司 | 唑烷酮-乙烯基稠合的-苯衍生物 |
| AU2003225669A1 (en) * | 2002-09-26 | 2004-04-19 | Pintex Pharmaceuticals, Inc. | Pin1-modulating compounds and methods of use thereof |
-
2003
- 2003-12-10 AU AU2003303231A patent/AU2003303231A1/en not_active Abandoned
- 2003-12-10 CA CA002510851A patent/CA2510851A1/en not_active Abandoned
- 2003-12-10 MX MXPA05006742A patent/MXPA05006742A/es not_active Application Discontinuation
- 2003-12-10 JP JP2004561828A patent/JP2006512357A/ja not_active Abandoned
- 2003-12-10 WO PCT/IB2003/005887 patent/WO2004056820A1/en not_active Ceased
- 2003-12-10 EP EP03813672A patent/EP1581529A1/en not_active Withdrawn
- 2003-12-10 BR BR0317572-3A patent/BR0317572A/pt not_active IP Right Cessation
- 2003-12-22 US US10/743,852 patent/US20040138199A1/en not_active Abandoned
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2012528165A (ja) * | 2009-05-26 | 2012-11-12 | エクセリクシス， インク． | ＰＩ３Ｋ／ｍＴＯＲの阻害剤としてのベンゾキサゼピンならびにそれらの使用および製造方法 |
| JP2013510825A (ja) * | 2009-11-13 | 2013-03-28 | メルク セローノ ソシエテ アノニム | 三環式ピラゾールアミン誘導体 |
| JP2015506344A (ja) * | 2011-12-22 | 2015-03-02 | ノバルティス アーゲー | ジヒドロ−ベンゾ−オキサジンおよびジヒドロ−ピリド−オキサジン誘導体 |
| US10532088B2 (en) | 2014-02-27 | 2020-01-14 | Lycera Corporation | Adoptive cellular therapy using an agonist of retinoic acid receptor-related orphan receptor gamma and related therapeutic methods |
| JP2017514855A (ja) * | 2014-05-05 | 2017-06-08 | リセラ・コーポレイションＬｙｃｅｒａ Ｃｏｒｐｏｒａｔｉｏｎ | ＲＯＲγアゴニストとして用いるテトラヒドロキノリンスルホンアミド及び関連化合物ならびに疾患の治療 |
| US10364237B2 (en) | 2014-05-05 | 2019-07-30 | Lycera Corporation | Tetrahydroquinoline sulfonamide and related compounds for use as agonists of RORγ and the treatment of disease |
| US10442798B2 (en) | 2014-05-05 | 2019-10-15 | Lycera Corporation | Tetrahydroquinoline sulfonamide and related compounds for use as agonists of RORγ and the treatment of disease |
| JP2017522300A (ja) * | 2014-06-30 | 2017-08-10 | アストラゼネカ・アクチエボラーグＡｓｔｒａｚｅｎｅｃａ Ａｋｔｉｅｂｏｌａｇ | 鉱質コルチコイド受容体修飾因子としてのベンゾオキサジノンアミド |
| US10421751B2 (en) | 2015-05-05 | 2019-09-24 | Lycera Corporation | Dihydro-2H-benzo[b][1,4]oxazine sulfonamide and related compounds for use as agonists of RORγ and the treatment of disease |
| US10611740B2 (en) | 2015-06-11 | 2020-04-07 | Lycera Corporation | Aryl dihydro-2H-benzo[b][1,4]oxazine sulfonamide and related compounds for use as agonists of RORγ and the treatment of disease |
| US11059796B2 (en) | 2015-06-11 | 2021-07-13 | The Regents Of The University Of Michigan | Aryl dihydro-2H benzo[b][1,4]oxazine sulfonamide and related compounds for use as agonists of RORγ and the treatment of disease |
Also Published As
| Publication number | Publication date |
|---|---|
| US20040138199A1 (en) | 2004-07-15 |
| MXPA05006742A (es) | 2005-09-08 |
| AU2003303231A1 (en) | 2004-07-14 |
| CA2510851A1 (en) | 2004-07-08 |
| BR0317572A (pt) | 2005-11-22 |
| EP1581529A1 (en) | 2005-10-05 |
| WO2004056820A1 (en) | 2004-07-08 |
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