AU2007243466B2 - Phosphoinositide 3-kinase inhibitor compounds and pharmaceutical compositions containing them - Google Patents
Phosphoinositide 3-kinase inhibitor compounds and pharmaceutical compositions containing them Download PDFInfo
- Publication number
- AU2007243466B2 AU2007243466B2 AU2007243466A AU2007243466A AU2007243466B2 AU 2007243466 B2 AU2007243466 B2 AU 2007243466B2 AU 2007243466 A AU2007243466 A AU 2007243466A AU 2007243466 A AU2007243466 A AU 2007243466A AU 2007243466 B2 AU2007243466 B2 AU 2007243466B2
- Authority
- AU
- Australia
- Prior art keywords
- indazol
- morpholinothieno
- pyrimidin
- methyl
- pyrimidine
- 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.)
- Ceased
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 229
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 32
- 239000002935 phosphatidylinositol 3 kinase inhibitor Substances 0.000 title description 2
- 229940043441 phosphoinositide 3-kinase inhibitor Drugs 0.000 title description 2
- 238000000034 method Methods 0.000 claims abstract description 150
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 83
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 52
- 108091000080 Phosphotransferase Proteins 0.000 claims abstract description 44
- 102000020233 phosphotransferase Human genes 0.000 claims abstract description 44
- 201000011510 cancer Diseases 0.000 claims abstract description 35
- 150000003839 salts Chemical class 0.000 claims abstract description 35
- 238000011282 treatment Methods 0.000 claims abstract description 34
- 239000002207 metabolite Substances 0.000 claims abstract description 24
- 239000012453 solvate Substances 0.000 claims abstract description 17
- 150000002632 lipids Chemical class 0.000 claims abstract description 16
- 230000002401 inhibitory effect Effects 0.000 claims abstract description 12
- 230000001575 pathological effect Effects 0.000 claims abstract description 9
- 230000001404 mediated effect Effects 0.000 claims abstract description 5
- -1 isopropylsulfonylamino, methylsulfonyl Chemical group 0.000 claims description 143
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 101
- 125000004943 pyrimidin-6-yl group Chemical group N1=CN=CC=C1* 0.000 claims description 92
- 125000000623 heterocyclic group Chemical group 0.000 claims description 83
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 74
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 68
- 125000001072 heteroaryl group Chemical group 0.000 claims description 57
- 125000000217 alkyl group Chemical group 0.000 claims description 52
- 125000003118 aryl group Chemical group 0.000 claims description 49
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 44
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- 201000010099 disease Diseases 0.000 claims description 39
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 38
- 125000004452 carbocyclyl group Chemical group 0.000 claims description 36
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 36
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 34
- RBNBDIMXFJYDLQ-UHFFFAOYSA-N thieno[3,2-d]pyrimidine Chemical compound C1=NC=C2SC=CC2=N1 RBNBDIMXFJYDLQ-UHFFFAOYSA-N 0.000 claims description 31
- 229920006395 saturated elastomer Polymers 0.000 claims description 28
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 27
- 125000002619 bicyclic group Chemical group 0.000 claims description 27
- 230000000694 effects Effects 0.000 claims description 27
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 25
- 125000000304 alkynyl group Chemical group 0.000 claims description 25
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- 239000003795 chemical substances by application Substances 0.000 claims description 24
- 125000003342 alkenyl group Chemical group 0.000 claims description 23
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
- HKSQZEGSMBFHGC-UHFFFAOYSA-N pyrimidine-4-carboxamide Chemical compound NC(=O)C1=CC=NC=N1 HKSQZEGSMBFHGC-UHFFFAOYSA-N 0.000 claims description 22
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 21
- 229910052799 carbon Inorganic materials 0.000 claims description 21
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 19
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- 241000282414 Homo sapiens Species 0.000 claims description 14
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 13
- 150000001412 amines Chemical class 0.000 claims description 13
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 11
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- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 9
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 9
- 206010012601 diabetes mellitus Diseases 0.000 claims description 9
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 9
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 9
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 9
- 125000006413 ring segment Chemical group 0.000 claims description 9
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
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- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 4
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- SILNNFMWIMZVEQ-UHFFFAOYSA-N 1,3-dihydrobenzimidazol-2-one Chemical compound C1=CC=C2NC(O)=NC2=C1 SILNNFMWIMZVEQ-UHFFFAOYSA-N 0.000 claims description 3
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 claims description 3
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- JYGWVCOFTZZSGS-UHFFFAOYSA-N methylsulfonylmethanamine Chemical compound CS(=O)(=O)CN JYGWVCOFTZZSGS-UHFFFAOYSA-N 0.000 claims description 3
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- RLZZZVKAURTHCP-UHFFFAOYSA-N phenanthrene-3,4-diol Chemical compound C1=CC=C2C3=C(O)C(O)=CC=C3C=CC2=C1 RLZZZVKAURTHCP-UHFFFAOYSA-N 0.000 claims description 3
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- 2007-04-24 US US11/789,427 patent/US7846929B2/en active Active
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- 2007-04-24 EP EP07776052.8A patent/EP2046799B1/en active Active
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- 2007-04-24 RU RU2008145662/04A patent/RU2437888C2/ru not_active IP Right Cessation
- 2007-04-24 MX MX2008013583A patent/MX2008013583A/es active IP Right Grant
- 2007-04-24 AU AU2007243466A patent/AU2007243466B2/en not_active Ceased
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- 2007-04-24 JP JP2009507753A patent/JP5291616B2/ja active Active
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Also Published As
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| ZA200810023B (en) | 2009-08-26 |
| CA2650295A1 (en) | 2007-11-08 |
| CL2007001166A1 (es) | 2008-01-25 |
| RU2008145662A (ru) | 2010-06-10 |
| US20110105464A1 (en) | 2011-05-05 |
| US20080039459A1 (en) | 2008-02-14 |
| IL194761A0 (en) | 2009-08-03 |
| CN101511840A (zh) | 2009-08-19 |
| WO2007127183A1 (en) | 2007-11-08 |
| RU2437888C2 (ru) | 2011-12-27 |
| KR20090024682A (ko) | 2009-03-09 |
| AR060632A1 (es) | 2008-07-02 |
| BRPI0710908A2 (pt) | 2012-06-26 |
| KR101402474B1 (ko) | 2014-06-19 |
| TW200801012A (en) | 2008-01-01 |
| EP2046799A1 (en) | 2009-04-15 |
| US8450315B2 (en) | 2013-05-28 |
| US7846929B2 (en) | 2010-12-07 |
| CA2650295C (en) | 2015-12-29 |
| EP2046799B1 (en) | 2017-07-19 |
| MX2008013583A (es) | 2008-10-31 |
| JP2009535335A (ja) | 2009-10-01 |
| JP5291616B2 (ja) | 2013-09-18 |
| NO20084927L (no) | 2009-01-23 |
| AU2007243466A1 (en) | 2007-11-08 |
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