CA2760791C - Heterocyclic compounds and uses thereof - Google Patents
Heterocyclic compounds and uses thereof Download PDFInfo
- Publication number
- CA2760791C CA2760791C CA2760791A CA2760791A CA2760791C CA 2760791 C CA2760791 C CA 2760791C CA 2760791 A CA2760791 A CA 2760791A CA 2760791 A CA2760791 A CA 2760791A CA 2760791 C CA2760791 C CA 2760791C
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- CA
- Canada
- Prior art keywords
- compound
- formula
- alkyl
- heteroaryl
- heterocycloalkyl
- Prior art date
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- 150000002391 heterocyclic compounds Chemical class 0.000 title description 2
- 108090000430 Phosphatidylinositol 3-kinases Proteins 0.000 claims abstract description 28
- 102000003993 Phosphatidylinositol 3-kinases Human genes 0.000 claims abstract description 22
- -1 heterocycloalkyloxy Chemical group 0.000 claims description 393
- 150000001875 compounds Chemical class 0.000 claims description 376
- 125000000217 alkyl group Chemical group 0.000 claims description 255
- 125000001072 heteroaryl group Chemical group 0.000 claims description 205
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 203
- 125000003118 aryl group Chemical group 0.000 claims description 193
- 229910052739 hydrogen Inorganic materials 0.000 claims description 172
- 239000001257 hydrogen Substances 0.000 claims description 172
- 125000005843 halogen group Chemical group 0.000 claims description 149
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 146
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 117
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical group NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 113
- 125000003342 alkenyl group Chemical group 0.000 claims description 103
- 125000000304 alkynyl group Chemical group 0.000 claims description 103
- 125000004122 cyclic group Chemical group 0.000 claims description 95
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 94
- 125000003368 amide group Chemical group 0.000 claims description 93
- 125000003545 alkoxy group Chemical group 0.000 claims description 92
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 86
- 229910052757 nitrogen Inorganic materials 0.000 claims description 83
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 80
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 80
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 80
- 125000004423 acyloxy group Chemical group 0.000 claims description 75
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 71
- 239000000203 mixture Substances 0.000 claims description 71
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 63
- 239000004202 carbamide Chemical group 0.000 claims description 59
- 229910019142 PO4 Inorganic materials 0.000 claims description 58
- 239000010452 phosphate Chemical group 0.000 claims description 58
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical group [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 57
- 125000002252 acyl group Chemical group 0.000 claims description 57
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical group [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 55
- 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 claims description 55
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 53
- 125000001424 substituent group Chemical group 0.000 claims description 47
- 150000003839 salts Chemical class 0.000 claims description 42
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 39
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 38
- 125000002950 monocyclic group Chemical group 0.000 claims description 27
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 25
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 23
- 238000011282 treatment Methods 0.000 claims description 20
- 108091007960 PI3Ks Proteins 0.000 claims description 18
- 206010028980 Neoplasm Diseases 0.000 claims description 17
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 claims description 16
- 210000004027 cell Anatomy 0.000 claims description 15
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 15
- 201000011510 cancer Diseases 0.000 claims description 14
- 239000007787 solid Substances 0.000 claims description 14
- JKZWPSHYNAEPAA-UHFFFAOYSA-N cyanocarbamic acid Chemical group OC(=O)NC#N JKZWPSHYNAEPAA-UHFFFAOYSA-N 0.000 claims description 11
- 239000007788 liquid Substances 0.000 claims description 11
- 101100495911 Arabidopsis thaliana CHR10 gene Proteins 0.000 claims description 10
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- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical compound NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 6
- 208000006673 asthma Diseases 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 6
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 5
- 239000000443 aerosol Substances 0.000 claims description 5
- 230000005764 inhibitory process Effects 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 208000023504 respiratory system disease Diseases 0.000 claims description 4
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- OGEBRHQLRGFBNV-RZDIXWSQSA-N chembl2036808 Chemical compound C12=NC(NCCCC)=NC=C2C(C=2C=CC(F)=CC=2)=NN1C[C@H]1CC[C@H](N)CC1 OGEBRHQLRGFBNV-RZDIXWSQSA-N 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- 230000002757 inflammatory effect Effects 0.000 claims description 3
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- 201000008482 osteoarthritis Diseases 0.000 claims description 3
- 208000020084 Bone disease Diseases 0.000 claims description 2
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- 208000007536 Thrombosis Diseases 0.000 claims description 2
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- 229940124597 therapeutic agent Drugs 0.000 claims description 2
- 201000003793 Myelodysplastic syndrome Diseases 0.000 claims 3
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- 208000003343 Antiphospholipid Syndrome Diseases 0.000 claims 2
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- 201000009273 Endometriosis Diseases 0.000 claims 1
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- 206010072579 Granulomatosis with polyangiitis Diseases 0.000 claims 1
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- 208000031671 Large B-Cell Diffuse Lymphoma Diseases 0.000 claims 1
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- 150000005829 chemical entities Chemical class 0.000 abstract description 5
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- VDBNYAPERZTOOF-UHFFFAOYSA-N isoquinolin-1(2H)-one Chemical compound C1=CC=C2C(=O)NC=CC2=C1 VDBNYAPERZTOOF-UHFFFAOYSA-N 0.000 abstract 1
- 150000002431 hydrogen Chemical group 0.000 description 130
- 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 32
- 125000004432 carbon atom Chemical group C* 0.000 description 31
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- RTKIYNMVFMVABJ-UHFFFAOYSA-L thimerosal Chemical compound [Na+].CC[Hg]SC1=CC=CC=C1C([O-])=O RTKIYNMVFMVABJ-UHFFFAOYSA-L 0.000 description 1
- 229940033663 thimerosal Drugs 0.000 description 1
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 description 1
- 210000001541 thymus gland Anatomy 0.000 description 1
- 210000001685 thyroid gland Anatomy 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 239000012049 topical pharmaceutical composition Substances 0.000 description 1
- 125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 description 1
- 239000003053 toxin Substances 0.000 description 1
- 231100000765 toxin Toxicity 0.000 description 1
- 210000003437 trachea Anatomy 0.000 description 1
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- 230000009466 transformation Effects 0.000 description 1
- 230000014616 translation Effects 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- WEAPVABOECTMGR-UHFFFAOYSA-N triethyl 2-acetyloxypropane-1,2,3-tricarboxylate Chemical compound CCOC(=O)CC(C(=O)OCC)(OC(C)=O)CC(=O)OCC WEAPVABOECTMGR-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 125000005455 trithianyl group Chemical group 0.000 description 1
- 230000005747 tumor angiogenesis Effects 0.000 description 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
- 125000001493 tyrosinyl group Chemical group [H]OC1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])(N([H])[H])C(*)=O 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
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- 230000002792 vascular Effects 0.000 description 1
- 230000004862 vasculogenesis Effects 0.000 description 1
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- 229910052727 yttrium Inorganic materials 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
Classifications
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
Landscapes
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
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| US17644909P | 2009-05-07 | 2009-05-07 | |
| US61/176,449 | 2009-05-07 | ||
| PCT/US2010/033939 WO2010129816A2 (en) | 2009-05-07 | 2010-05-06 | Heterocyclic compounds and uses thereof |
Publications (2)
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| CA2760791A1 CA2760791A1 (en) | 2010-11-11 |
| CA2760791C true CA2760791C (en) | 2017-06-20 |
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| CA2760791A Active CA2760791C (en) | 2009-05-07 | 2010-05-06 | Heterocyclic compounds and uses thereof |
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| EP (1) | EP2427195B1 (enExample) |
| JP (1) | JP5789252B2 (enExample) |
| CA (1) | CA2760791C (enExample) |
| WO (1) | WO2010129816A2 (enExample) |
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| KR20150038395A (ko) | 2006-04-04 | 2015-04-08 | 더 리젠트스 오브 더 유니이버시티 오브 캘리포니아 | 키나제 길항물질 |
| PL2137186T3 (pl) | 2007-03-23 | 2016-09-30 | Związki heterocykliczne i ich zastosowania | |
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| JP5789252B2 (ja) | 2015-10-07 |
| EP2427195A2 (en) | 2012-03-14 |
| EP2427195B1 (en) | 2019-05-01 |
| US8785454B2 (en) | 2014-07-22 |
| EP2427195A4 (en) | 2015-04-01 |
| US20120329776A1 (en) | 2012-12-27 |
| JP2012526143A (ja) | 2012-10-25 |
| WO2010129816A2 (en) | 2010-11-11 |
| US9315505B2 (en) | 2016-04-19 |
| WO2010129816A3 (en) | 2014-03-20 |
| CA2760791A1 (en) | 2010-11-11 |
| US20140296207A1 (en) | 2014-10-02 |
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