MXPA05006742A

MXPA05006742A - Benzoxazinas y derivados de las mismas como inhibidores de fosfoinositido-3-quinasas.

Benzoxazinas y derivados de las mismas como inhibidores de fosfoinositido-3-quinasas.

Info

Publication number: MXPA05006742A
Authority: MX; Mexico
Prior art keywords: thioxo; dihydro; thiazolidin; phenyl; oxo
Prior art date: 2002-12-20

Application number

MXPA05006742A

Other languages

English (en)

Spanish (es)

Inventor

Melean Visnick

Original Assignee

Warner Lambert Co

Priority date

2002-12-20

Filing date

2003-12-10

Publication date

2005-09-08

2003-12-10 Application filed by Warner Lambert Co filed Critical Warner Lambert Co

2005-09-08 Publication of MXPA05006742A publication Critical patent/MXPA05006742A/es

Links

239000003112 inhibitor Substances 0.000 title description 14
150000005130 benzoxazines Chemical class 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims abstract description 163
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 42
150000003839 salts Chemical class 0.000 claims abstract description 27
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 alkyiC.6 Chemical group 0.000 claims description 174
125000000217 alkyl group Chemical group 0.000 claims description 39
208000035475 disorder Diseases 0.000 claims description 29
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 23
239000002253 acid Substances 0.000 claims description 22
230000001404 mediated effect Effects 0.000 claims description 21
125000001624 naphthyl group Chemical group 0.000 claims description 15
229910052731 fluorine Inorganic materials 0.000 claims description 14
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
229910052799 carbon Inorganic materials 0.000 claims description 12
229910052801 chlorine Inorganic materials 0.000 claims description 11
229910052739 hydrogen Inorganic materials 0.000 claims description 11
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 10
125000003342 alkenyl group Chemical group 0.000 claims description 10
239000003937 drug carrier Substances 0.000 claims description 8
229910052757 nitrogen Inorganic materials 0.000 claims description 8
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
229910052760 oxygen Inorganic materials 0.000 claims description 7
MNFPITABCLMULF-UHFFFAOYSA-N 6-[(4-oxo-2-sulfanylidene-1,3-thiazolidin-5-ylidene)methyl]-2,3-dihydro-1,4-benzoxazine-4-carboxylic acid Chemical compound C1=C2N(C(=O)O)CCOC2=CC=C1C=C1SC(=S)NC1=O MNFPITABCLMULF-UHFFFAOYSA-N 0.000 claims description 5
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 5
125000004450 alkenylene group Chemical group 0.000 claims description 5
125000002619 bicyclic group Chemical group 0.000 claims description 5
206010039073 rheumatoid arthritis Diseases 0.000 claims description 5
229910052717 sulfur Inorganic materials 0.000 claims description 5
201000008482 osteoarthritis Diseases 0.000 claims description 4
125000003386 piperidinyl group Chemical group 0.000 claims description 4
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
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
206010002556 Ankylosing Spondylitis Diseases 0.000 claims description 3
208000023275 Autoimmune disease Diseases 0.000 claims description 3
108091007960 PI3Ks Proteins 0.000 claims description 3
125000004601 benzofurazanyl group Chemical group N1=C2C(=NO1)C(=CC=C2)* 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
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 2
125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
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 2
102000010400 1-phosphatidylinositol-3-kinase activity proteins Human genes 0.000 claims 2
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
SDYWXFYBZPNOFX-UHFFFAOYSA-N 3,4-dichloroaniline Chemical compound NC1=CC=C(Cl)C(Cl)=C1 SDYWXFYBZPNOFX-UHFFFAOYSA-N 0.000 claims 1
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 1
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 1
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 1
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 1
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 1
238000011282 treatment Methods 0.000 abstract description 18
201000010099 disease Diseases 0.000 abstract description 13
208000024172 Cardiovascular disease Diseases 0.000 abstract description 4
229910052700 potassium Inorganic materials 0.000 abstract description 3
201000011529 cardiovascular cancer Diseases 0.000 abstract description 2
239000000543 intermediate Substances 0.000 description 54
239000000203 mixture Substances 0.000 description 39
238000006243 chemical reaction Methods 0.000 description 36
125000000592 heterocycloalkyl group Chemical group 0.000 description 36
238000004452 microanalysis Methods 0.000 description 36
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
239000000047 product Substances 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 29
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 21
238000000034 method Methods 0.000 description 20
125000004432 carbon atom Chemical group C* 0.000 description 17
210000004027 cell Anatomy 0.000 description 16
239000011541 reaction mixture Substances 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
108090000623 proteins and genes Proteins 0.000 description 14
QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 13
125000000753 cycloalkyl group Chemical group 0.000 description 13
238000002360 preparation method Methods 0.000 description 13
102000004169 proteins and genes Human genes 0.000 description 13
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 12
125000006580 bicyclic heterocycloalkyl group Chemical group 0.000 description 12
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
FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 12
230000002829 reductive effect Effects 0.000 description 12
239000003826 tablet Substances 0.000 description 12
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
125000002252 acyl group Chemical group 0.000 description 11
239000000460 chlorine Substances 0.000 description 11
230000000694 effects Effects 0.000 description 11
238000009472 formulation Methods 0.000 description 11
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 11
125000002950 monocyclic group Chemical group 0.000 description 11
239000012074 organic phase Substances 0.000 description 11
229910000027 potassium carbonate Inorganic materials 0.000 description 11
239000012267 brine Substances 0.000 description 10
238000009833 condensation Methods 0.000 description 10
230000005494 condensation Effects 0.000 description 10
125000001072 heteroaryl group Chemical group 0.000 description 10
235000011181 potassium carbonates Nutrition 0.000 description 10
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 10
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DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 9
229910052794 bromium Inorganic materials 0.000 description 9
229940088598 enzyme Drugs 0.000 description 9
125000005842 heteroatom Chemical group 0.000 description 9
229910052740 iodine Inorganic materials 0.000 description 9
KIWUVOGUEXMXSV-UHFFFAOYSA-N rhodanine Chemical compound O=C1CSC(=S)N1 KIWUVOGUEXMXSV-UHFFFAOYSA-N 0.000 description 9
239000007787 solid Substances 0.000 description 9
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
102000004190 Enzymes Human genes 0.000 description 8
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239000002904 solvent Substances 0.000 description 8
241000701447 unidentified baculovirus Species 0.000 description 8
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 7
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101710189301 101 kDa malaria antigen Proteins 0.000 description 6
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102100026478 Phosphoinositide 3-kinase regulatory subunit 5 Human genes 0.000 description 6
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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 6
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HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
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239000011780 sodium chloride Substances 0.000 description 6
125000001424 substituent group Chemical group 0.000 description 6
239000003981 vehicle Substances 0.000 description 6
HKWJHKSHEWVOSS-OMDJCSNQSA-N 1,2-dihexadecanoyl-sn-glycero-3-phospho-(1D-myo-inositol-3,4-bisphosphate) Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@@H](OC(=O)CCCCCCCCCCCCCCC)COP(O)(=O)O[C@H]1[C@H](O)[C@@H](O)[C@H](OP(O)(O)=O)[C@@H](OP(O)(O)=O)[C@H]1O HKWJHKSHEWVOSS-OMDJCSNQSA-N 0.000 description 5
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229910000104 sodium hydride Inorganic materials 0.000 description 5
238000003756 stirring Methods 0.000 description 5
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GCSVNNODDIEGEX-UHFFFAOYSA-N 2-sulfanylidene-1,3-oxazolidin-4-one Chemical compound O=C1COC(=S)N1 GCSVNNODDIEGEX-UHFFFAOYSA-N 0.000 description 4
WRDABNWSWOHGMS-UHFFFAOYSA-N AEBSF hydrochloride Chemical compound Cl.NCCC1=CC=C(S(F)(=O)=O)C=C1 WRDABNWSWOHGMS-UHFFFAOYSA-N 0.000 description 4
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