KR20140063605A - 헤테로사이클릭 화합물 및 그의 용도 - Google Patents
헤테로사이클릭 화합물 및 그의 용도 Download PDFInfo
- Publication number
- KR20140063605A KR20140063605A KR1020147004100A KR20147004100A KR20140063605A KR 20140063605 A KR20140063605 A KR 20140063605A KR 1020147004100 A KR1020147004100 A KR 1020147004100A KR 20147004100 A KR20147004100 A KR 20147004100A KR 20140063605 A KR20140063605 A KR 20140063605A
- Authority
- KR
- South Korea
- Prior art keywords
- alkyl
- cycloalkyl
- formula
- substituted
- heteroaryl
- 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.)
- Withdrawn
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- 150000002391 heterocyclic compounds Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 302
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 73
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 36
- 201000010099 disease Diseases 0.000 claims abstract description 31
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 12
- 201000011510 cancer Diseases 0.000 claims abstract description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 271
- 125000001072 heteroaryl group Chemical group 0.000 claims description 233
- 125000003118 aryl group Chemical group 0.000 claims description 217
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 208
- -1 cyano, hydroxyl Chemical group 0.000 claims description 204
- 125000000623 heterocyclic group Chemical group 0.000 claims description 183
- 125000000304 alkynyl group Chemical group 0.000 claims description 152
- 125000003342 alkenyl group Chemical group 0.000 claims description 144
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 129
- 239000000203 mixture Substances 0.000 claims description 127
- 229910052739 hydrogen Inorganic materials 0.000 claims description 121
- 239000001257 hydrogen Substances 0.000 claims description 120
- 125000003545 alkoxy group Chemical group 0.000 claims description 108
- 125000005843 halogen group Chemical group 0.000 claims description 105
- 150000002431 hydrogen Chemical class 0.000 claims description 93
- 238000000034 method Methods 0.000 claims description 86
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 86
- 125000002252 acyl group Chemical group 0.000 claims description 85
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 80
- 125000003368 amide group Chemical group 0.000 claims description 78
- 125000001424 substituent group Chemical group 0.000 claims description 78
- 125000004423 acyloxy group Chemical group 0.000 claims description 77
- 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 claims description 74
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 68
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 56
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 51
- 125000001188 haloalkyl group Chemical group 0.000 claims description 49
- 229910052757 nitrogen Inorganic materials 0.000 claims description 47
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 45
- 108091007960 PI3Ks Proteins 0.000 claims description 41
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 41
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 38
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 36
- 125000004122 cyclic group Chemical group 0.000 claims description 34
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 31
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 28
- 239000004202 carbamide Substances 0.000 claims description 28
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 27
- 229910019142 PO4 Inorganic materials 0.000 claims description 26
- 125000004043 oxo group Chemical group O=* 0.000 claims description 26
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 25
- 239000010452 phosphate Substances 0.000 claims description 25
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 23
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 23
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 20
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 20
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 15
- 239000011574 phosphorus Substances 0.000 claims description 15
- 229910052698 phosphorus Inorganic materials 0.000 claims description 15
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 13
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 13
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 13
- RGICCULPCWNRAB-UHFFFAOYSA-N 2-[2-(2-hexoxyethoxy)ethoxy]ethanol Chemical compound CCCCCCOCCOCCOCCO RGICCULPCWNRAB-UHFFFAOYSA-N 0.000 claims description 12
- 125000004076 pyridyl group Chemical group 0.000 claims description 11
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 11
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 10
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- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 7
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 7
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- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 6
- 125000005844 heterocyclyloxy group Chemical group 0.000 claims description 6
- 230000001404 mediated effect Effects 0.000 claims description 6
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- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 5
- 208000023275 Autoimmune disease Diseases 0.000 claims description 3
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 3
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 3
- 102000010400 1-phosphatidylinositol-3-kinase activity proteins Human genes 0.000 claims 1
- 102000003993 Phosphatidylinositol 3-kinases Human genes 0.000 abstract description 86
- 108090000430 Phosphatidylinositol 3-kinases Proteins 0.000 abstract description 86
- 238000011282 treatment Methods 0.000 abstract description 10
- 229910052799 carbon Inorganic materials 0.000 description 68
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 62
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 60
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- 150000003254 radicals Chemical class 0.000 description 48
- 125000005842 heteroatom Chemical group 0.000 description 40
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- 125000004432 carbon atom Chemical group C* 0.000 description 33
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 31
- 125000005885 heterocycloalkylalkyl group Chemical group 0.000 description 31
- 229940002612 prodrug Drugs 0.000 description 31
- 239000000651 prodrug Substances 0.000 description 31
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 30
- 150000003839 salts Chemical class 0.000 description 29
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 28
- 125000004429 atom Chemical group 0.000 description 26
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- 229930195729 fatty acid Natural products 0.000 description 26
- 239000000194 fatty acid Substances 0.000 description 26
- 235000013877 carbamide Nutrition 0.000 description 24
- 125000004452 carbocyclyl group Chemical group 0.000 description 23
- 239000003795 chemical substances by application Substances 0.000 description 23
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical group CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
- 238000009472 formulation Methods 0.000 description 22
- 235000021317 phosphate Nutrition 0.000 description 22
- 229920001223 polyethylene glycol Polymers 0.000 description 22
- 125000006413 ring segment Chemical group 0.000 description 21
- 239000004094 surface-active agent Substances 0.000 description 21
- 239000002904 solvent Substances 0.000 description 20
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 19
- 125000002877 alkyl aryl group Chemical group 0.000 description 18
- 229910052760 oxygen Inorganic materials 0.000 description 18
- 239000004480 active ingredient Substances 0.000 description 17
- 239000001301 oxygen Substances 0.000 description 17
- 239000002202 Polyethylene glycol Substances 0.000 description 16
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 16
- 125000004104 aryloxy group Chemical group 0.000 description 16
- 125000005884 carbocyclylalkyl group Chemical group 0.000 description 16
- 235000019441 ethanol Nutrition 0.000 description 16
- 239000003755 preservative agent Substances 0.000 description 16
- 239000007788 liquid Substances 0.000 description 15
- 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 description 15
- 229910052717 sulfur Chemical group 0.000 description 15
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 14
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 14
- 125000004414 alkyl thio group Chemical group 0.000 description 14
- 239000003814 drug Substances 0.000 description 14
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- 108090000623 proteins and genes Proteins 0.000 description 14
- 239000011593 sulfur Chemical group 0.000 description 14
- 125000001544 thienyl group Chemical group 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 239000002552 dosage form Substances 0.000 description 13
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- 230000000694 effects Effects 0.000 description 12
- 235000011187 glycerol Nutrition 0.000 description 12
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- 125000001786 isothiazolyl group Chemical group 0.000 description 12
- 102000020233 phosphotransferase Human genes 0.000 description 12
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- 238000003419 tautomerization reaction Methods 0.000 description 12
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 11
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 11
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical class OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 11
- 125000004438 haloalkoxy group Chemical group 0.000 description 11
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- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 10
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- 125000000547 substituted alkyl group Chemical group 0.000 description 10
- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 10
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- 230000002401 inhibitory effect Effects 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 9
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Classifications
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- 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
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- 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
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
- 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
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- Organic Chemistry (AREA)
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- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
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- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Immunology (AREA)
- Epidemiology (AREA)
- Transplantation (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (5)
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| US201161509441P | 2011-07-19 | 2011-07-19 | |
| US61/509,441 | 2011-07-19 | ||
| US201261622251P | 2012-04-10 | 2012-04-10 | |
| US61/622,251 | 2012-04-10 | ||
| PCT/US2012/047190 WO2013012918A1 (en) | 2011-07-19 | 2012-07-18 | Heterocyclic compounds and uses thereof |
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| JP (1) | JP6027611B2 (enExample) |
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| AU (1) | AU2012284091B2 (enExample) |
| CA (1) | CA2842190A1 (enExample) |
| HK (1) | HK1198475A1 (enExample) |
| IL (1) | IL230536A0 (enExample) |
| MX (1) | MX2014000648A (enExample) |
| TW (1) | TWI565709B (enExample) |
| WO (1) | WO2013012918A1 (enExample) |
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| CA2635581C (en) | 2005-12-28 | 2017-02-28 | Vertex Pharmaceuticals Incorporated | Solid forms of n-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide |
| US9365634B2 (en) * | 2007-05-29 | 2016-06-14 | Angiochem Inc. | Aprotinin-like polypeptides for delivering agents conjugated thereto to tissues |
| DK2240451T3 (da) | 2008-01-04 | 2017-11-20 | Intellikine Llc | Isoquinolinonderivater substitueret med en purin, der er anvendelig som pi3k-inhibitorer |
| US8193182B2 (en) | 2008-01-04 | 2012-06-05 | Intellikine, Inc. | Substituted isoquinolin-1(2H)-ones, and methods of use thereof |
| AU2009238187B2 (en) | 2008-04-18 | 2014-03-06 | Angiochem Inc. | Pharmaceutical compositions of paclitaxel, paclitaxel analogs or paclitaxel conjugates and related methods of preparation and use |
| CA2738429C (en) | 2008-09-26 | 2016-10-25 | Intellikine, Inc. | Heterocyclic kinase inhibitors |
| CA2740316A1 (en) | 2008-10-15 | 2010-04-22 | Angiochem Inc. | Conjugates of glp-1 agonists and uses thereof |
| CA2740317A1 (en) | 2008-10-15 | 2010-04-22 | Angiochem Inc. | Etoposide and doxorubicin conjugates for drug delivery |
| CA2745524C (en) | 2008-12-05 | 2020-06-09 | Angiochem Inc. | Conjugates of neurotensin or neurotensin analogs and uses thereof |
| BRPI0922611A2 (pt) | 2008-12-17 | 2018-11-06 | Angiochem Inc | inibidores de metaloproteína de matriz de membrana tipo 1 e usos dos mesmos |
| US9173891B2 (en) | 2009-04-20 | 2015-11-03 | Angiochem, Inc. | Treatment of ovarian cancer using an anticancer agent conjugated to an angiopep-2 analog |
| EP2427195B1 (en) | 2009-05-07 | 2019-05-01 | Intellikine, LLC | Heterocyclic compounds and uses thereof |
| EP2448965A4 (en) | 2009-07-02 | 2015-02-11 | Angiochem Inc | MULTIMEPEPTID CONJUGATES AND ITS USES |
| AU2011255218B2 (en) | 2010-05-21 | 2015-03-12 | Infinity Pharmaceuticals, Inc. | Chemical compounds, compositions and methods for kinase modulation |
| EA201890869A3 (ru) | 2010-06-03 | 2019-03-29 | Фармасайкликс, Инк. | Применение ингибиторов тирозинкиназы брутона (btk) |
| AU2011326427B2 (en) | 2010-11-10 | 2016-01-07 | Infinity Pharmaceuticals Inc. | Heterocyclic compounds and uses thereof |
| PE20180318A1 (es) | 2011-01-10 | 2018-02-09 | Infinity Pharmaceuticals Inc | Procedimiento para preparar isoquinolinonas y formas solidas de isoquinolinonas |
| EP2481500A1 (de) | 2011-01-31 | 2012-08-01 | Stopinc Aktiengesellschaft | Verschlussplatte sowie ein Schiebenverschluss am Ausguss eines Metallschmelze enthaltenden Behälters |
| WO2013012915A1 (en) | 2011-07-19 | 2013-01-24 | Infinity Pharmaceuticals Inc. | Heterocyclic compounds and uses thereof |
| WO2013012918A1 (en) | 2011-07-19 | 2013-01-24 | Infinity Pharmaceuticals Inc. | Heterocyclic compounds and uses thereof |
| AR091790A1 (es) | 2011-08-29 | 2015-03-04 | Infinity Pharmaceuticals Inc | Derivados de isoquinolin-1-ona y sus usos |
| US8940742B2 (en) * | 2012-04-10 | 2015-01-27 | Infinity Pharmaceuticals, Inc. | Heterocyclic compounds and uses thereof |
| US8828998B2 (en) | 2012-06-25 | 2014-09-09 | Infinity Pharmaceuticals, Inc. | Treatment of lupus, fibrotic conditions, and inflammatory myopathies and other disorders using PI3 kinase inhibitors |
| WO2014018567A1 (en) | 2012-07-24 | 2014-01-30 | Pharmacyclics, Inc. | Mutations associated with resistance to inhibitors of bruton's tyrosine kinase (btk) |
| LT2914296T (lt) | 2012-11-01 | 2018-09-25 | Infinity Pharmaceuticals, Inc. | Vėžio gydymas, panaudojant p13 kinazės izoformos moduliatorius |
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| EP3003309B1 (en) | 2013-05-30 | 2020-09-09 | Infinity Pharmaceuticals, Inc. | Treatment of cancers using pi3 kinase isoform modulators |
| JO3368B1 (ar) | 2013-06-04 | 2019-03-13 | Janssen Pharmaceutica Nv | مركبات 6، 7- ثاني هيدرو بيرازولو [5،1-a] بيرازين- 4 (5 يد)- اون واستخدامها بصفة منظمات تفارغية سلبية لمستقبلات ميجلور 2 |
| CA2920059A1 (en) | 2013-09-22 | 2015-03-26 | Calitor Sciences, Llc | Substituted aminopyrimidine compounds and methods of use |
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| WO2015051244A1 (en) * | 2013-10-04 | 2015-04-09 | Infinity Pharmaceuticals, Inc. | Heterocyclic compounds and uses thereof |
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| AR098776A1 (es) * | 2013-12-18 | 2016-06-15 | Chiesi Farm Spa | Derivados del isocromeno como inhibidores de las fosfoinositido-3 quinasas |
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| CA2942528A1 (en) | 2014-03-20 | 2015-09-24 | Pharmacyclics Inc. | Phospholipase c gamma 2 and resistance associated mutations |
| UY36060A (es) | 2014-04-02 | 2015-10-30 | Bayer Pharma AG | Compuestos de azol sustituidos con amida |
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| JOP20150179B1 (ar) | 2014-08-01 | 2021-08-17 | Janssen Pharmaceutica Nv | مركبات 6 ، 7 ثاني هيدرو بيرازولو [ 1، 5 الفا ] بيرازين – 4 (5 يد) – اون واستخدامها كمنظمات الوسترية سلبية لمستقبلات ملجور 2 |
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| LT3179991T (lt) | 2014-08-11 | 2021-11-10 | Acerta Pharma B.V. | Terapiniai btk inhibitoriaus ir bcl-2 inhibitoriaus deriniai |
| WO2016024232A1 (en) | 2014-08-11 | 2016-02-18 | Acerta Pharma B.V. | Therapeutic combinations of a btk inhibitor, a pi3k inhibitor, a jak-2 inhibitor and/or a cdk 4/6 inhibitor |
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| KR20170063954A (ko) | 2014-10-07 | 2017-06-08 | 버텍스 파마슈티칼스 인코포레이티드 | 낭성 섬유증 막횡단 전도도 조절자의 조정제의 공-결정 |
| WO2016087489A1 (en) | 2014-12-03 | 2016-06-09 | Janssen Pharmaceutica Nv | Radiolabelled mglur2 pet ligands |
| AU2015357167B2 (en) | 2014-12-03 | 2020-06-25 | Janssen Pharmaceutica Nv | 6,7-dihydropyrazolo(1,5-alpha)pyrazin-4(5H)-one compounds and their use as negative allosteric modulators of mGluR2 receptors |
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| EP3389728B1 (en) | 2015-12-18 | 2020-08-05 | Janssen Pharmaceutica NV | Radiolabelled mglur2/3 pet ligands |
| PL3389727T3 (pl) | 2015-12-18 | 2021-02-08 | Janssen Pharmaceutica Nv | RADIOZNAKOWANE LIGANDY mGluR2/3 DO PET |
| CN118994191A (zh) | 2016-02-05 | 2024-11-22 | 戴纳立制药公司 | 受体相互作用蛋白激酶1的抑制剂 |
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| UA125216C2 (uk) | 2016-06-24 | 2022-02-02 | Інфініті Фармасьютікалз, Інк. | Комбінована терапія |
| IT201600070952A1 (it) * | 2016-07-07 | 2018-01-07 | Univ Degli Studi Di Ferrara | NUOVI TIAZOLO[5,4-d]PIRIMIDIN DERIVATI QUALI AGONISTI INVERSI DEI RECETTORI A2A DELL’ADENOSINA |
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-
2012
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- 2012-07-18 JP JP2014521731A patent/JP6027611B2/ja not_active Expired - Fee Related
- 2012-07-18 US US13/552,473 patent/US9056877B2/en active Active
- 2012-07-18 AR ARP120102605A patent/AR088218A1/es unknown
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- 2012-07-18 MX MX2014000648A patent/MX2014000648A/es unknown
- 2012-07-18 TW TW101125905A patent/TWI565709B/zh not_active IP Right Cessation
- 2012-07-18 KR KR1020147004100A patent/KR20140063605A/ko not_active Withdrawn
- 2012-07-18 HK HK14111976.9A patent/HK1198475A1/xx unknown
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Also Published As
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| US20150246932A1 (en) | 2015-09-03 |
| HK1198475A1 (en) | 2015-05-08 |
| US20130029984A1 (en) | 2013-01-31 |
| CA2842190A1 (en) | 2013-01-24 |
| MX2014000648A (es) | 2014-09-25 |
| AU2012284091A1 (en) | 2013-03-21 |
| EP2734530A1 (en) | 2014-05-28 |
| AU2012284091B2 (en) | 2015-11-12 |
| CN103946226A (zh) | 2014-07-23 |
| US9056877B2 (en) | 2015-06-16 |
| US9605003B2 (en) | 2017-03-28 |
| IL230536A0 (en) | 2014-03-31 |
| TW201311700A (zh) | 2013-03-16 |
| AR088218A1 (es) | 2014-05-21 |
| JP2014520888A (ja) | 2014-08-25 |
| WO2013012918A1 (en) | 2013-01-24 |
| TWI565709B (zh) | 2017-01-11 |
| JP6027611B2 (ja) | 2016-11-16 |
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