CN102333779B - 苯并吡喃和苯并氧杂*pi3k抑制剂化合物和使用方法 - Google Patents
苯并吡喃和苯并氧杂*pi3k抑制剂化合物和使用方法 Download PDFInfo
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- CN102333779B CN102333779B CN200980120112.8A CN200980120112A CN102333779B CN 102333779 B CN102333779 B CN 102333779B CN 200980120112 A CN200980120112 A CN 200980120112A CN 102333779 B CN102333779 B CN 102333779B
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- thieno
- oxa
- dihydrobenzo
- cancer
- methyl
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- 0 *c1nc(-c2c(*)c(*)c(*)c(*)c2OCC2)c2[s]1 Chemical compound *c1nc(-c2c(*)c(*)c(*)c(*)c2OCC2)c2[s]1 0.000 description 34
- FYHLXZNEQOUKQO-UHFFFAOYSA-N Brc1cc(CCOc2cccnc2-2)c-2[s]1 Chemical compound Brc1cc(CCOc2cccnc2-2)c-2[s]1 FYHLXZNEQOUKQO-UHFFFAOYSA-N 0.000 description 1
- ZJNVNROFRFMFIN-UHFFFAOYSA-N Brc1ccc(-c2c(CCO3)[s]c(-[n]4nncc4C4CC4)n2)c3c1 Chemical compound Brc1ccc(-c2c(CCO3)[s]c(-[n]4nncc4C4CC4)n2)c3c1 ZJNVNROFRFMFIN-UHFFFAOYSA-N 0.000 description 1
- NNXROHRFMWHXNH-UHFFFAOYSA-N CC(O1)=NNC1=O Chemical compound CC(O1)=NNC1=O NNXROHRFMWHXNH-UHFFFAOYSA-N 0.000 description 1
- FFDPQXZPWFYPPW-UHFFFAOYSA-N CC1=N[NH+](C)[N-]N1C Chemical compound CC1=N[NH+](C)[N-]N1C FFDPQXZPWFYPPW-UHFFFAOYSA-N 0.000 description 1
- JPSXCQLATZXBEK-UHFFFAOYSA-N CCCC(CC)CC(NC1)=NNC1=O Chemical compound CCCC(CC)CC(NC1)=NNC1=O JPSXCQLATZXBEK-UHFFFAOYSA-N 0.000 description 1
- ZRHBPNUFYLTFPT-UHFFFAOYSA-N CN(C(c1cc(CCOc2cc(Br)ccc2-2)c-2[s]1)=O)c(c(Cl)c1)ccc1C(N1CCN(C)CC1)=O Chemical compound CN(C(c1cc(CCOc2cc(Br)ccc2-2)c-2[s]1)=O)c(c(Cl)c1)ccc1C(N1CCN(C)CC1)=O ZRHBPNUFYLTFPT-UHFFFAOYSA-N 0.000 description 1
- OCEWBETVYYBBBI-UHFFFAOYSA-N CN(C(c1cc(CCOc2cc(C(O)=O)ccc2-2)c-2[s]1)=O)c1ccccc1Cl Chemical compound CN(C(c1cc(CCOc2cc(C(O)=O)ccc2-2)c-2[s]1)=O)c1ccccc1Cl OCEWBETVYYBBBI-UHFFFAOYSA-N 0.000 description 1
- OPKCZGPVBYJGIV-UHFFFAOYSA-N CN(C(c1cc(CCOc2cc(C(OC)=O)ccc2-2)c-2[s]1)=O)c(cccc1)c1Cl Chemical compound CN(C(c1cc(CCOc2cc(C(OC)=O)ccc2-2)c-2[s]1)=O)c(cccc1)c1Cl OPKCZGPVBYJGIV-UHFFFAOYSA-N 0.000 description 1
- XOXGCCVJVNFACH-UHFFFAOYSA-N CN(C(c1cc(COc(c-2c3)ccc3C(OC)=O)c-2[s]1)=O)c(ccc(F)c1)c1F Chemical compound CN(C(c1cc(COc(c-2c3)ccc3C(OC)=O)c-2[s]1)=O)c(ccc(F)c1)c1F XOXGCCVJVNFACH-UHFFFAOYSA-N 0.000 description 1
- WKBLWORJCNMCBJ-UHFFFAOYSA-N CN(C)C(c(cc1Cl)ccc1N(C)C(c1cc(CCOc2cc(C(OC)=O)ccc2-2)c-2[s]1)=O)=O Chemical compound CN(C)C(c(cc1Cl)ccc1N(C)C(c1cc(CCOc2cc(C(OC)=O)ccc2-2)c-2[s]1)=O)=O WKBLWORJCNMCBJ-UHFFFAOYSA-N 0.000 description 1
- NQQURCVYDZGIKC-UHFFFAOYSA-N CN(C)C(c(cc1Cl)ccc1N)=O Chemical compound CN(C)C(c(cc1Cl)ccc1N)=O NQQURCVYDZGIKC-UHFFFAOYSA-N 0.000 description 1
- NMDCDNDSQSQFNR-UHFFFAOYSA-N CN(C)C(c(cc1I)ccc1N(C)C(c1cc(CCOc2cc(Br)ccc2-2)c-2[s]1)=O)=O Chemical compound CN(C)C(c(cc1I)ccc1N(C)C(c1cc(CCOc2cc(Br)ccc2-2)c-2[s]1)=O)=O NMDCDNDSQSQFNR-UHFFFAOYSA-N 0.000 description 1
- QYINYMBAYUKKIT-UHFFFAOYSA-N CN(C1=O)N=C(c2cc(CCOc3cc(C(OC)=O)ccc3-3)c-3[s]2)N1c1ccccc1Cl Chemical compound CN(C1=O)N=C(c2cc(CCOc3cc(C(OC)=O)ccc3-3)c-3[s]2)N1c1ccccc1Cl QYINYMBAYUKKIT-UHFFFAOYSA-N 0.000 description 1
- HLYPJXWUQFWTPY-UHFFFAOYSA-N Cc1n[o]nc1N(C)C Chemical compound Cc1n[o]nc1N(C)C HLYPJXWUQFWTPY-UHFFFAOYSA-N 0.000 description 1
- FRAKGJKEMLMXMD-UHFFFAOYSA-N Cc1ncn[n]1C Chemical compound Cc1ncn[n]1C FRAKGJKEMLMXMD-UHFFFAOYSA-N 0.000 description 1
- VGRVPVRIDACDMR-UHFFFAOYSA-N Ic1cnccc1OCCc1c[s]cc1 Chemical compound Ic1cnccc1OCCc1c[s]cc1 VGRVPVRIDACDMR-UHFFFAOYSA-N 0.000 description 1
- WFAWKYDSYSGUBC-UHFFFAOYSA-N O=C(NN=C1c2cc(CCOc3cc(Br)ccc3-3)c-3[s]2)N1c(cccc1)c1Cl Chemical compound O=C(NN=C1c2cc(CCOc3cc(Br)ccc3-3)c-3[s]2)N1c(cccc1)c1Cl WFAWKYDSYSGUBC-UHFFFAOYSA-N 0.000 description 1
- BRPOEOGAOWQGPF-UHFFFAOYSA-N O=C(c1cc(CCOc2c-3ccc(Br)c2)c-3[s]1)Nc1ccccc1Cl Chemical compound O=C(c1cc(CCOc2c-3ccc(Br)c2)c-3[s]1)Nc1ccccc1Cl BRPOEOGAOWQGPF-UHFFFAOYSA-N 0.000 description 1
- RGYGEONYZWHGIA-UHFFFAOYSA-N O=C(c1cc(COc(c-2c3)ccc3Br)c-2[s]1)Nc(c(F)c1)ccc1F Chemical compound O=C(c1cc(COc(c-2c3)ccc3Br)c-2[s]1)Nc(c(F)c1)ccc1F RGYGEONYZWHGIA-UHFFFAOYSA-N 0.000 description 1
- SNYYCMUSGFCUHA-UHFFFAOYSA-N OC(c(nc1-2)ccc1OCCc1c-2[s]c(-c2ncn[n]2-c(ccc(F)c2)c2F)c1)=O Chemical compound OC(c(nc1-2)ccc1OCCc1c-2[s]c(-c2ncn[n]2-c(ccc(F)c2)c2F)c1)=O SNYYCMUSGFCUHA-UHFFFAOYSA-N 0.000 description 1
- UAMKDURBCGBZGZ-UHFFFAOYSA-N OC(c1cc(CCOc2cc(Br)ccc2-2)c-2[s]1)=O Chemical compound OC(c1cc(CCOc2cc(Br)ccc2-2)c-2[s]1)=O UAMKDURBCGBZGZ-UHFFFAOYSA-N 0.000 description 1
- MSTXEKWAOXKOPN-UHFFFAOYSA-N OC(c1cc(CCOc2cccnc2-2)c-2[s]1)=O Chemical compound OC(c1cc(CCOc2cccnc2-2)c-2[s]1)=O MSTXEKWAOXKOPN-UHFFFAOYSA-N 0.000 description 1
- CDIIIMBWGUPDTJ-UHFFFAOYSA-N OC(c1ccc(-c2c(CCO3)cc(-c4ncn[n]4-c(ccc(F)c4)c4F)[s]2)c3c1)=O Chemical compound OC(c1ccc(-c2c(CCO3)cc(-c4ncn[n]4-c(ccc(F)c4)c4F)[s]2)c3c1)=O CDIIIMBWGUPDTJ-UHFFFAOYSA-N 0.000 description 1
- LHDAMAKAICZPOS-UHFFFAOYSA-N OCCc1c[nH]cc1 Chemical compound OCCc1c[nH]cc1 LHDAMAKAICZPOS-UHFFFAOYSA-N 0.000 description 1
- ICTIDHOYLQAYIC-UHFFFAOYSA-N S=C(c1cc(CCOc2c-3ccc(Br)c2)c-3[s]1)Nc1ccccc1Cl Chemical compound S=C(c1cc(CCOc2c-3ccc(Br)c2)c-3[s]1)Nc1ccccc1Cl ICTIDHOYLQAYIC-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/38—Heterocyclic compounds having sulfur as a ring hetero atom
- A61K31/381—Heterocyclic compounds having sulfur as a ring hetero atom having five-membered rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
- A61K31/4155—1,2-Diazoles non condensed and containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4196—1,2,4-Triazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4245—Oxadiazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
- A61K31/427—Thiazoles not condensed and containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
- A61K31/429—Thiazoles condensed with heterocyclic ring systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
- A61K31/4365—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system having sulfur as a ring hetero atom, e.g. ticlopidine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4436—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a heterocyclic ring having sulfur as a ring hetero atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/53—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with three nitrogens as the only ring hetero atoms, e.g. chlorazanil, melamine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
- C07D495/14—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains three hetero rings
- C07D513/14—Ortho-condensed systems
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Organic Chemistry (AREA)
- Epidemiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oncology (AREA)
- Hematology (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US4082708P | 2008-03-31 | 2008-03-31 | |
| US61/040827 | 2008-03-31 | ||
| US10222008P | 2008-10-02 | 2008-10-02 | |
| US61/102220 | 2008-10-02 | ||
| PCT/US2009/038795 WO2009123971A1 (en) | 2008-03-31 | 2009-03-30 | Benzopyran and benzoxepin pi3k inhibitor compounds and methods of use |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN102333779A CN102333779A (zh) | 2012-01-25 |
| CN102333779B true CN102333779B (zh) | 2015-12-09 |
Family
ID=40790991
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN200980120112.8A Active CN102333779B (zh) | 2008-03-31 | 2009-03-30 | 苯并吡喃和苯并氧杂*pi3k抑制剂化合物和使用方法 |
Country Status (21)
| Country | Link |
|---|---|
| US (4) | US7928248B2 (enExample) |
| EP (1) | EP2276767B1 (enExample) |
| JP (1) | JP5511786B2 (enExample) |
| KR (1) | KR101626996B1 (enExample) |
| CN (1) | CN102333779B (enExample) |
| AR (1) | AR071112A1 (enExample) |
| AU (1) | AU2009231885B2 (enExample) |
| BR (1) | BRPI0910346A2 (enExample) |
| CA (1) | CA2719032C (enExample) |
| CL (1) | CL2009000780A1 (enExample) |
| DK (1) | DK2276767T3 (enExample) |
| ES (1) | ES2480994T3 (enExample) |
| IL (1) | IL208359A (enExample) |
| MX (1) | MX2010010659A (enExample) |
| PE (1) | PE20091720A1 (enExample) |
| PL (1) | PL2276767T3 (enExample) |
| RU (1) | RU2506267C2 (enExample) |
| SI (1) | SI2276767T1 (enExample) |
| TW (1) | TWI443102B (enExample) |
| WO (1) | WO2009123971A1 (enExample) |
| ZA (1) | ZA201007218B (enExample) |
Families Citing this family (56)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2250160B1 (en) | 2008-01-25 | 2015-11-11 | Millennium Pharmaceuticals, Inc. | Thiophenes and their use as phosphatidylinositol 3-kinase (pi3k) inhibitors |
| WO2009123971A1 (en) | 2008-03-31 | 2009-10-08 | Genentech, Inc. | Benzopyran and benzoxepin pi3k inhibitor compounds and methods of use |
| US9090601B2 (en) | 2009-01-30 | 2015-07-28 | Millennium Pharmaceuticals, Inc. | Thiazole derivatives |
| US8796314B2 (en) | 2009-01-30 | 2014-08-05 | Millennium Pharmaceuticals, Inc. | Heteroaryls and uses thereof |
| WO2010090716A1 (en) | 2009-01-30 | 2010-08-12 | Millennium Pharmaceuticals, Inc. | Heteroaryls and their use as pi3k inhibitors |
| US20100233733A1 (en) * | 2009-02-10 | 2010-09-16 | Nodality, Inc., A Delaware Corporation | Multiple mechanisms for modulation of the pi3 kinase pathway |
| EA201200087A1 (ru) * | 2009-07-02 | 2012-07-30 | Новартис Аг | 2-карбоксамиды циклоаминомочевин, которые являются ингибиторами pi3k |
| RU2600927C2 (ru) | 2009-09-28 | 2016-10-27 | Ф.Хоффманн-Ля Рош Аг | Бензоксазепиновые ингибиторы pi3k и способы применения |
| PE20140918A1 (es) * | 2009-09-28 | 2014-08-06 | Hoffmann La Roche | Compuestos de benzoxepina inhibidores de la pi3k |
| WO2011049625A1 (en) | 2009-10-20 | 2011-04-28 | Mansour Samadpour | Method for aflatoxin screening of products |
| EP2493866A1 (en) * | 2009-10-29 | 2012-09-05 | Bristol-Myers Squibb Company | Tricyclic heterocyclic compounds |
| PT2496567T (pt) | 2009-11-05 | 2017-11-15 | Rhizen Pharmaceuticals S A | Novos moduladores de quinase benzopiran |
| US9073940B2 (en) | 2009-11-13 | 2015-07-07 | Merck Serono Sa | Tricyclic pyrazol amine derivatives |
| WO2011063126A1 (en) * | 2009-11-18 | 2011-05-26 | Satoshi Ohtake | Highly dispersible powders, compositions and methods for preparation |
| US9062038B2 (en) | 2010-08-11 | 2015-06-23 | Millennium Pharmaceuticals, Inc. | Heteroaryls and uses thereof |
| WO2012021615A1 (en) | 2010-08-11 | 2012-02-16 | Millennium Pharmaceuticals, Inc. | Heteroaryls and uses thereof |
| UY33554A (es) | 2010-08-11 | 2012-02-29 | Millennium Pharm Inc | Heteroarilos y usos de los mismos |
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