CA2510851A1

CA2510851A1 - Benzoxazines and derivatives thereof as inhibitors of pi3ks

Benzoxazines and derivatives thereof as inhibitors of pi3ks Download PDF

Info

Publication number: CA2510851A1
Authority: CA; Canada
Prior art keywords: thioxo; dihydro; thiazolidin; compound; phenyl
Prior art date: 2002-12-20
Legal status : Abandoned

Application number

CA002510851A

Other languages

English (en)

French (fr)

Inventor

Rocco Dean Gogliotti

Keri Lynn Muccioli

Kimberly Suzanne Para

Melean Visnick

Current Assignee

Warner Lambert Co LLC

Original Assignee

Individual

Priority date

2002-12-20

Filing date

2003-12-10

Publication date

2004-07-08

2003-12-10 Application filed by Individual filed Critical Individual

2004-07-08 Publication of CA2510851A1 publication Critical patent/CA2510851A1/en

Status Abandoned legal-status Critical Current

Links

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
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