CA2510851A1 - Benzoxazines and derivatives thereof as inhibitors of pi3ks - Google Patents

Info

Publication number

CA2510851A1

CA2510851A1 CA002510851A CA2510851A CA2510851A1 CA 2510851 A1 CA2510851 A1 CA 2510851A1 CA 002510851 A CA002510851 A CA 002510851A CA 2510851 A CA2510851 A CA 2510851A CA 2510851 A1 CA2510851 A1 CA 2510851A1

Authority

CA

Canada

Prior art keywords

thioxo

dihydro

thiazolidin

compound

phenyl

Prior art date

2002-12-20

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

• Espacenet
• Global Dossier
• CIPO
• Discuss

• 239000003112 inhibitor Substances 0.000 title description 13
• 150000005130 benzoxazines Chemical class 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 166
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 44
• 150000003839 salts Chemical class 0.000 claims abstract description 27
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 19
• 208000027866 inflammatory disease Diseases 0.000 claims abstract description 9
• 229910052727 yttrium Inorganic materials 0.000 claims abstract description 3
• -1 4-pyridinyl Chemical group 0.000 claims description 133
• 108091007960 PI3Ks Proteins 0.000 claims description 60
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 36
• 208000035475 disorder Diseases 0.000 claims description 32
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 23
• 230000001404 mediated effect Effects 0.000 claims description 22
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
• 125000001624 naphthyl group Chemical group 0.000 claims description 17
• 125000006580 bicyclic heterocycloalkyl group Chemical group 0.000 claims description 14
• 239000005977 Ethylene Substances 0.000 claims description 13
• 229910052739 hydrogen Inorganic materials 0.000 claims description 11
• 229910052799 carbon Inorganic materials 0.000 claims description 10
• 125000001072 heteroaryl group Chemical group 0.000 claims description 9
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
• 239000003814 drug Substances 0.000 claims description 7
• 239000003937 drug carrier Substances 0.000 claims description 7
• 206010039073 rheumatoid arthritis Diseases 0.000 claims description 7
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 6
• 125000006545 (C1-C9) alkyl group Chemical group 0.000 claims description 6
• 125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 6
• 229910052757 nitrogen Inorganic materials 0.000 claims description 6
• 201000008482 osteoarthritis Diseases 0.000 claims description 6
• 229910052760 oxygen Inorganic materials 0.000 claims description 6
• 229910052717 sulfur Inorganic materials 0.000 claims description 6
• 206010002556 Ankylosing Spondylitis Diseases 0.000 claims description 5
• 208000023275 Autoimmune disease Diseases 0.000 claims description 5
• 125000000449 nitro group Chemical group [O-][N+](*)=O 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
• 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
• 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
• 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 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
• 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
• 238000004519 manufacturing process Methods 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
• 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 2
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 3
• 102000010400 1-phosphatidylinositol-3-kinase activity proteins Human genes 0.000 claims 3
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 2
• 238000011282 treatment Methods 0.000 abstract description 18
• 201000010099 disease Diseases 0.000 abstract description 12
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• 229910052700 potassium Inorganic materials 0.000 abstract description 3
• 201000011529 cardiovascular cancer Diseases 0.000 abstract description 2
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• 102000038030 PI3Ks Human genes 0.000 description 46
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• 239000000243 solution Substances 0.000 description 29
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• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 25
• 125000000217 alkyl group Chemical group 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
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• 125000000753 cycloalkyl group Chemical group 0.000 description 20
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