CA2817577A1 - Heterocyclic compounds and uses thereof - Google Patents
Heterocyclic compounds and uses thereof Download PDFInfo
- Publication number
- CA2817577A1 CA2817577A1 CA2817577A CA2817577A CA2817577A1 CA 2817577 A1 CA2817577 A1 CA 2817577A1 CA 2817577 A CA2817577 A CA 2817577A CA 2817577 A CA2817577 A CA 2817577A CA 2817577 A1 CA2817577 A1 CA 2817577A1
- Authority
- CA
- Canada
- Prior art keywords
- compound
- alkyl
- heteroaryl
- aryl
- heterocycloalkyl
- 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.)
- Abandoned
Links
- 150000002391 heterocyclic compounds Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 317
- 108090000430 Phosphatidylinositol 3-kinases Proteins 0.000 claims abstract description 88
- 102000003993 Phosphatidylinositol 3-kinases Human genes 0.000 claims abstract description 88
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 69
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 50
- 238000000034 method Methods 0.000 claims abstract description 47
- 238000011282 treatment Methods 0.000 claims abstract description 16
- -1 heterocycloalkyloxy Chemical group 0.000 claims description 429
- 125000000217 alkyl group Chemical group 0.000 claims description 251
- 125000001072 heteroaryl group Chemical group 0.000 claims description 216
- 125000003118 aryl group Chemical group 0.000 claims description 180
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 179
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 154
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 146
- 229910052739 hydrogen Inorganic materials 0.000 claims description 141
- 239000001257 hydrogen Substances 0.000 claims description 141
- 125000005843 halogen group Chemical group 0.000 claims description 130
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 114
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical group NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 108
- 125000003342 alkenyl group Chemical group 0.000 claims description 104
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 98
- 125000004122 cyclic group Chemical group 0.000 claims description 96
- 229910052757 nitrogen Inorganic materials 0.000 claims description 93
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 91
- 125000003368 amide group Chemical group 0.000 claims description 89
- 125000003545 alkoxy group Chemical group 0.000 claims description 87
- 125000000304 alkynyl group Chemical group 0.000 claims description 86
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 86
- 125000001424 substituent group Chemical group 0.000 claims description 84
- 125000004423 acyloxy group Chemical group 0.000 claims description 80
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 69
- 125000002252 acyl group Chemical group 0.000 claims description 66
- 229910019142 PO4 Inorganic materials 0.000 claims description 61
- 239000010452 phosphate Chemical group 0.000 claims description 61
- 239000004202 carbamide Chemical group 0.000 claims description 59
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical group [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 58
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical group [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 58
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 55
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 49
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 42
- 125000001188 haloalkyl group Chemical group 0.000 claims description 38
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 38
- 229910052799 carbon Inorganic materials 0.000 claims description 36
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 34
- 150000003457 sulfones Chemical group 0.000 claims description 31
- GTVCVBGHHUYLMO-UHFFFAOYSA-N trithiazetidine 1,1,2-trioxide Chemical group S1(=O)(=O)NSS1=O GTVCVBGHHUYLMO-UHFFFAOYSA-N 0.000 claims description 31
- 125000002950 monocyclic group Chemical group 0.000 claims description 29
- 101000585507 Solanum tuberosum Cytochrome b-c1 complex subunit 7 Proteins 0.000 claims description 28
- 208000035475 disorder Diseases 0.000 claims description 28
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 26
- 125000002947 alkylene group Chemical group 0.000 claims description 24
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 24
- 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 claims description 23
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 22
- 125000005885 heterocycloalkylalkyl group Chemical group 0.000 claims description 22
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 19
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 16
- 206010028980 Neoplasm Diseases 0.000 claims description 15
- 230000002401 inhibitory effect Effects 0.000 claims description 14
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 13
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- 108091007960 PI3Ks Proteins 0.000 claims description 11
- 125000005844 heterocyclyloxy group Chemical group 0.000 claims description 11
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 claims description 10
- 125000004474 heteroalkylene group Chemical group 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 7
- 239000005977 Ethylene Substances 0.000 claims description 7
- 125000001153 fluoro group Chemical group F* 0.000 claims description 7
- 230000001404 mediated effect Effects 0.000 claims description 6
- 208000023275 Autoimmune disease Diseases 0.000 claims description 5
- 208000027866 inflammatory disease Diseases 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 229940124597 therapeutic agent Drugs 0.000 claims description 4
- 102000038030 PI3Ks Human genes 0.000 claims description 3
- 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
- CDGFEINVQHEUQV-UHFFFAOYSA-N [1,3]thiazolo[5,4-d]pyrimidine Chemical compound N1=CN=C2SC=NC2=C1 CDGFEINVQHEUQV-UHFFFAOYSA-N 0.000 claims description 2
- LDIJKUBTLZTFRG-UHFFFAOYSA-N pyrazolo[1,5-a]pyrimidine Chemical compound N1=CC=CN2N=CC=C21 LDIJKUBTLZTFRG-UHFFFAOYSA-N 0.000 claims description 2
- BWESROVQGZSBRX-UHFFFAOYSA-N pyrido[3,2-d]pyrimidine Chemical compound C1=NC=NC2=CC=CN=C21 BWESROVQGZSBRX-UHFFFAOYSA-N 0.000 claims description 2
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 claims description 2
- 101100495911 Arabidopsis thaliana CHR10 gene Proteins 0.000 claims 3
- JKZWPSHYNAEPAA-UHFFFAOYSA-N cyanocarbamic acid Chemical compound OC(=O)NC#N JKZWPSHYNAEPAA-UHFFFAOYSA-N 0.000 claims 1
- 125000004475 heteroaralkyl group Chemical group 0.000 claims 1
- VTVRXITWWZGKHV-UHFFFAOYSA-N imidazo[1,2-b]pyridazine Chemical compound N1=CC=CC2=NC=CN21 VTVRXITWWZGKHV-UHFFFAOYSA-N 0.000 claims 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
- 201000010099 disease Diseases 0.000 abstract description 22
- 108091000080 Phosphotransferase Proteins 0.000 abstract description 21
- 102000020233 phosphotransferase Human genes 0.000 abstract description 21
- 230000000694 effects Effects 0.000 abstract description 17
- 150000002431 hydrogen Chemical group 0.000 description 95
- 239000000203 mixture Substances 0.000 description 77
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 67
- 125000005842 heteroatom Chemical group 0.000 description 54
- 125000004432 carbon atom Chemical group C* 0.000 description 46
- 235000014698 Brassica juncea var multisecta Nutrition 0.000 description 43
- 244000275904 brauner Senf Species 0.000 description 43
- 125000000623 heterocyclic group Chemical group 0.000 description 36
- 229940002612 prodrug Drugs 0.000 description 32
- 239000000651 prodrug Substances 0.000 description 32
- 150000003839 salts Chemical class 0.000 description 30
- 150000003254 radicals Chemical class 0.000 description 29
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 26
- 125000006413 ring segment Chemical group 0.000 description 26
- 125000004429 atom Chemical group 0.000 description 25
- 125000003386 piperidinyl group Chemical group 0.000 description 25
- 125000000168 pyrrolyl group Chemical group 0.000 description 25
- 125000002757 morpholinyl group Chemical group 0.000 description 24
- 125000004076 pyridyl group Chemical group 0.000 description 24
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 23
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 23
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 23
- 125000004193 piperazinyl group Chemical group 0.000 description 23
- 239000003795 chemical substances by application Substances 0.000 description 22
- 229910052760 oxygen Inorganic materials 0.000 description 22
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 22
- 108010029485 Protein Isoforms Proteins 0.000 description 21
- 102000001708 Protein Isoforms Human genes 0.000 description 21
- 239000001301 oxygen Chemical group 0.000 description 21
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 20
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 19
- 125000001309 chloro group Chemical group Cl* 0.000 description 19
- 125000003709 fluoroalkyl group Chemical group 0.000 description 19
- 125000002883 imidazolyl group Chemical group 0.000 description 19
- 230000000670 limiting effect Effects 0.000 description 19
- 125000003226 pyrazolyl group Chemical group 0.000 description 19
- 229910052717 sulfur Inorganic materials 0.000 description 19
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 19
- 125000004452 carbocyclyl group Chemical group 0.000 description 18
- 125000005884 carbocyclylalkyl group Chemical group 0.000 description 18
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 18
- 239000011593 sulfur Substances 0.000 description 18
- 125000000335 thiazolyl group Chemical group 0.000 description 18
- 125000001544 thienyl group Chemical group 0.000 description 18
- 125000003373 pyrazinyl group Chemical group 0.000 description 17
- 125000000714 pyrimidinyl group Chemical group 0.000 description 17
- 239000004094 surface-active agent Substances 0.000 description 17
- 239000004480 active ingredient Substances 0.000 description 16
- 125000002393 azetidinyl group Chemical group 0.000 description 16
- 125000002541 furyl group Chemical group 0.000 description 16
- 102000004169 proteins and genes Human genes 0.000 description 16
- 108090000623 proteins and genes Proteins 0.000 description 16
- 125000002098 pyridazinyl group Chemical group 0.000 description 16
- 239000012453 solvate Substances 0.000 description 16
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 16
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 15
- 125000000547 substituted alkyl group Chemical group 0.000 description 15
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 15
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 14
- 239000000969 carrier Substances 0.000 description 14
- 210000004027 cell Anatomy 0.000 description 14
- 235000014113 dietary fatty acids Nutrition 0.000 description 14
- 239000002552 dosage form Substances 0.000 description 14
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- 239000000194 fatty acid Substances 0.000 description 14
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 14
- 125000001041 indolyl group Chemical group 0.000 description 14
- 108090000765 processed proteins & peptides Proteins 0.000 description 14
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 14
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 14
- 125000004306 triazinyl group Chemical group 0.000 description 14
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 13
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 13
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 13
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 12
- 230000008901 benefit Effects 0.000 description 12
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 12
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 12
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 12
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- 238000002360 preparation method Methods 0.000 description 12
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- 125000004568 thiomorpholinyl group Chemical group 0.000 description 12
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- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 11
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- NCAIGTHBQTXTLR-UHFFFAOYSA-N phentermine hydrochloride Chemical compound [Cl-].CC(C)([NH3+])CC1=CC=CC=C1 NCAIGTHBQTXTLR-UHFFFAOYSA-N 0.000 description 8
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/26—Heterocyclic compounds containing purine ring systems with an oxygen, sulphur, or nitrogen atom directly attached in position 2 or 6, but not in both
- C07D473/32—Nitrogen atom
- C07D473/34—Nitrogen atom attached in position 6, e.g. adenine
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- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
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- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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
- C07D401/02—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 two hetero rings
- C07D401/12—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 two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- 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
-
- 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
- C07D513/02—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 two hetero rings
- C07D513/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Immunology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
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- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Transplantation (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic 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)
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| US41238410P | 2010-11-10 | 2010-11-10 | |
| US61/412,384 | 2010-11-10 | ||
| US201161509454P | 2011-07-19 | 2011-07-19 | |
| US61/509,454 | 2011-07-19 | ||
| PCT/US2011/060212 WO2012064973A2 (en) | 2010-11-10 | 2011-11-10 | Heterocyclic compounds and uses thereof |
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| CA (1) | CA2817577A1 (enExample) |
| WO (1) | WO2012064973A2 (enExample) |
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| DE10238722A1 (de) | 2002-08-23 | 2004-03-11 | Bayer Ag | Selektive Phosphodiesterase 9A-Inhibitoren als Arzneimittel zur Verbesserung kognitiver Prozesse |
| ATE512674T1 (de) | 2003-01-06 | 2011-07-15 | Angiochem Inc | Angiopep-1, verwandte verbindungen, und deren verwnedungen |
| US8044060B2 (en) | 2003-05-09 | 2011-10-25 | Boehringer Ingelheim International Gmbh | 6-cyclylmethyl- and 6-alkylmethyl pyrazolo[3,4-D]pyrimidines, methods for their preparation and methods for their use to treat impairments of perception, concentration learning and/or memory |
| DE10320785A1 (de) | 2003-05-09 | 2004-11-25 | Bayer Healthcare Ag | 6-Arylmethyl-substituierte Pyrazolopyrimidine |
| EP1699527A1 (en) | 2004-01-02 | 2006-09-13 | Advanced Cardiovascular Systems, Inc. | High-density lipoprotein coated medical devices |
| US9365634B2 (en) | 2007-05-29 | 2016-06-14 | Angiochem Inc. | Aprotinin-like polypeptides for delivering agents conjugated thereto to tissues |
| US8193182B2 (en) | 2008-01-04 | 2012-06-05 | Intellikine, Inc. | Substituted isoquinolin-1(2H)-ones, and methods of use thereof |
| CN104926815B (zh) | 2008-01-04 | 2017-11-03 | 英特利凯恩有限责任公司 | 某些化学实体、组合物和方法 |
| UA105362C2 (en) | 2008-04-02 | 2014-05-12 | Бьорингер Ингельхайм Интернациональ Гмбх | 1-heterocyclyl-1, 5-dihydro-pyrazolo [3, 4-d] pyrimidin-4-one derivatives and their use as pde9a modulators |
| WO2009127072A1 (en) | 2008-04-18 | 2009-10-22 | Angiochem Inc. | Pharmaceutical compositions of paclitaxel, paclitaxel analogs or paclitaxel conjugates and related methods of preparation and use |
| JP5731978B2 (ja) | 2008-09-26 | 2015-06-10 | インテリカイン， エルエルシー | 複素環キナーゼ阻害剤 |
| WO2010043049A1 (en) | 2008-10-15 | 2010-04-22 | Angiochem Inc. | Etoposide and doxorubicin conjugates for drug delivery |
| AU2009304560A1 (en) | 2008-10-15 | 2010-04-22 | Angiochem Inc. | Conjugates of GLP-1 agonists and uses thereof |
| CA2745524C (en) | 2008-12-05 | 2020-06-09 | Angiochem Inc. | Conjugates of neurotensin or neurotensin analogs and uses thereof |
| AU2009327267A1 (en) | 2008-12-17 | 2011-07-14 | Angiochem, Inc. | Membrane type-1 matrix metalloprotein inhibitors and uses thereof |
| AU2010230290B2 (en) | 2009-03-31 | 2013-03-14 | Boehringer Ingelheim International Gmbh | 1-heterocyclyl-1, 5-dihydro-pyrazolo [3, 4-d] pyrimidin-4-one derivatives and their use as PDE9A modulators |
| AU2010239069B2 (en) | 2009-04-20 | 2015-05-14 | Angiochem Inc | Treatment of ovarian cancer using an anticancer agent conjugated to an Angiopep-2 analog |
| JP5789252B2 (ja) | 2009-05-07 | 2015-10-07 | インテリカイン， エルエルシー | 複素環式化合物およびその使用 |
| SG177384A1 (en) | 2009-06-29 | 2012-02-28 | Incyte Corp | Pyrimidinones as pi3k inhibitors |
| WO2011000095A1 (en) | 2009-07-02 | 2011-01-06 | Angiochem Inc. | Multimeric peptide conjugates and uses thereof |
| US8759359B2 (en) | 2009-12-18 | 2014-06-24 | Incyte Corporation | Substituted heteroaryl fused derivatives as PI3K inhibitors |
| JP5816678B2 (ja) | 2010-04-14 | 2015-11-18 | インサイト・コーポレイションＩｎｃｙｔｅ Ｃｏｒｐｏｒａｔｉｏｎ | ＰＩ３Ｋδ阻害剤としての縮合誘導体 |
| JP5951600B2 (ja) | 2010-05-21 | 2016-07-13 | インフィニティー ファーマシューティカルズ， インコーポレイテッド | キナーゼ調節のための、化合物、組成物および方法 |
| WO2011163195A1 (en) | 2010-06-21 | 2011-12-29 | Incyte Corporation | Fused pyrrole derivatives as pi3k inhibitors |
| JP2013545749A (ja) * | 2010-11-10 | 2013-12-26 | インフィニティー ファーマシューティカルズ， インコーポレイテッド | 複素環化合物及びその使用 |
| CA2822070C (en) | 2010-12-20 | 2019-09-17 | Incyte Corporation | N-(1-(substituted-phenyl)ethyl)-9h-purin-6-amines as pi3k inhibitors |
| US8933119B2 (en) | 2011-01-03 | 2015-01-13 | The William M. Yarbrough Foundation | Method for treating phytophotodermatitis |
| US10308599B2 (en) | 2011-01-03 | 2019-06-04 | The William M. Yarbrough Foundation | Isothiocyanate functional surfactants, formulations incorporating the same, and associated methods of use |
| US9962361B2 (en) | 2011-01-03 | 2018-05-08 | The William M. Yarbrough Foundation | Isothiocyanate functional surfactants, formulations incorporating the same, and associated methods of use |
| US10647668B2 (en) | 2011-01-03 | 2020-05-12 | The William M. Yarbrough Foundation | Isothiocyanate functional surfactant and associated method of use |
| US11407713B2 (en) | 2011-01-03 | 2022-08-09 | The William M. Yarbrough Foundation | Isothiocyanate functional surfactants, formulations incorporating the same, and associated methods of use |
| US10640464B2 (en) | 2011-01-03 | 2020-05-05 | The William M. Yarbrough Foundation | Use of isothiocyanate functional surfactants as Nrf2 inducers to treat epidermolysis bullosa simplex and related diseases |
| US10273205B2 (en) | 2011-01-03 | 2019-04-30 | The William M. Yarbrough Foundation | Isothiocyanate functional surfactants, formulations incorporating isothiocyanate functional surfactants and associated methods for treating biofilms |
| US11279674B2 (en) | 2011-01-03 | 2022-03-22 | The William M. Yarbrough Foundation | Isothiocyanate functional surfactant and associated method of use |
| TWI674262B (zh) | 2011-01-10 | 2019-10-11 | 美商英菲尼提製藥股份有限公司 | 製備異喹啉酮之方法及異喹啉酮之固體形式 |
| US8865765B2 (en) | 2011-01-12 | 2014-10-21 | The William M. Yarbrough Foundation | Method for treating eczema |
| US9532969B2 (en) | 2011-02-08 | 2017-01-03 | The William M. Yarbrough Foundation | Method for treating psoriasis |
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| WO2012064973A3 (en) | 2012-07-26 |
| US8901133B2 (en) | 2014-12-02 |
| CN103298474B (zh) | 2016-06-29 |
| AU2011326427A9 (en) | 2016-02-04 |
| US20120122838A1 (en) | 2012-05-17 |
| US20150031672A1 (en) | 2015-01-29 |
| EP2637669A2 (en) | 2013-09-18 |
| AU2011326427A1 (en) | 2013-05-02 |
| CN103298474A (zh) | 2013-09-11 |
| AU2011326427B2 (en) | 2016-01-07 |
| US9388183B2 (en) | 2016-07-12 |
| WO2012064973A2 (en) | 2012-05-18 |
| EP2637669A4 (en) | 2014-04-02 |
| JP2013545749A (ja) | 2013-12-26 |
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