JP5936609B2 - キナーゼインヒビターの経口製剤 - Google Patents
キナーゼインヒビターの経口製剤 Download PDFInfo
- Publication number
- JP5936609B2 JP5936609B2 JP2013518572A JP2013518572A JP5936609B2 JP 5936609 B2 JP5936609 B2 JP 5936609B2 JP 2013518572 A JP2013518572 A JP 2013518572A JP 2013518572 A JP2013518572 A JP 2013518572A JP 5936609 B2 JP5936609 B2 JP 5936609B2
- Authority
- JP
- Japan
- Prior art keywords
- formulation
- item
- kinase inhibitor
- weight
- polyethylene glycol
- 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.)
- Expired - Fee Related
Links
- 229940043355 kinase inhibitor Drugs 0.000 title claims description 30
- 239000003757 phosphotransferase inhibitor Substances 0.000 title claims description 30
- 238000002360 preparation method Methods 0.000 title description 2
- 239000000203 mixture Substances 0.000 claims description 80
- 238000009472 formulation Methods 0.000 claims description 70
- 150000001875 compounds Chemical class 0.000 claims description 20
- -1 Caprylate ester Chemical class 0.000 claims description 14
- 229940113116 polyethylene glycol 1000 Drugs 0.000 claims description 12
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 claims description 12
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 claims description 11
- 239000000787 lecithin Substances 0.000 claims description 11
- 235000010445 lecithin Nutrition 0.000 claims description 11
- 229940067606 lecithin Drugs 0.000 claims description 11
- 229920002565 Polyethylene Glycol 400 Polymers 0.000 claims description 10
- 229940080812 glyceryl caprate Drugs 0.000 claims description 8
- LKUNXBRZDFMZOK-UHFFFAOYSA-N rac-1-monodecanoylglycerol Chemical compound CCCCCCCCCC(=O)OCC(O)CO LKUNXBRZDFMZOK-UHFFFAOYSA-N 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- 229940087068 glyceryl caprylate Drugs 0.000 claims description 7
- JLFNLZLINWHATN-UHFFFAOYSA-N pentaethylene glycol Chemical compound OCCOCCOCCOCCOCCO JLFNLZLINWHATN-UHFFFAOYSA-N 0.000 claims description 5
- 210000001035 gastrointestinal tract Anatomy 0.000 claims description 4
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- 108091000080 Phosphotransferase Proteins 0.000 description 11
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- 102000020233 phosphotransferase Human genes 0.000 description 11
- 229920001223 polyethylene glycol Polymers 0.000 description 10
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 9
- GHBFNMLVSPCDGN-UHFFFAOYSA-N rac-1-monooctanoylglycerol Chemical compound CCCCCCCC(=O)OCC(O)CO GHBFNMLVSPCDGN-UHFFFAOYSA-N 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
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- ZAKOWWREFLAJOT-ADUHFSDSSA-N [2,5,7,8-tetramethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydrochromen-6-yl] acetate Chemical group CC(=O)OC1=C(C)C(C)=C2OC(CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C ZAKOWWREFLAJOT-ADUHFSDSSA-N 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
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- 125000001072 heteroaryl group Chemical group 0.000 description 6
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- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 5
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- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 4
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 4
- 230000005764 inhibitory process Effects 0.000 description 4
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- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 4
- 208000024891 symptom Diseases 0.000 description 4
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- 125000002669 linoleoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 229940057917 medium chain triglycerides Drugs 0.000 description 3
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- IIMIOEBMYPRQGU-UHFFFAOYSA-L picoplatin Chemical compound N.[Cl-].[Cl-].[Pt+2].CC1=CC=CC=N1 IIMIOEBMYPRQGU-UHFFFAOYSA-L 0.000 description 3
- 229950005566 picoplatin Drugs 0.000 description 3
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 3
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 3
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- 230000001225 therapeutic effect Effects 0.000 description 3
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 3
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 2
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 2
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 2
- 239000005642 Oleic acid Substances 0.000 description 2
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 2
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- 230000004712 cancer cell adhesion Effects 0.000 description 2
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- 239000003995 emulsifying agent Substances 0.000 description 2
- 125000001033 ether group Chemical group 0.000 description 2
- 210000002744 extracellular matrix Anatomy 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 2
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-M octanoate Chemical compound CCCCCCCC([O-])=O WWZKQHOCKIZLMA-UHFFFAOYSA-M 0.000 description 2
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
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- 229920000642 polymer Polymers 0.000 description 2
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- IFFLKGMDBKQMAH-UHFFFAOYSA-N 2,4-diaminopyridine Chemical class NC1=CC=NC(N)=C1 IFFLKGMDBKQMAH-UHFFFAOYSA-N 0.000 description 1
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- 239000005632 Capric acid (CAS 334-48-5) Substances 0.000 description 1
- 239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 description 1
- 241000282693 Cercopithecidae Species 0.000 description 1
- 102000004266 Collagen Type IV Human genes 0.000 description 1
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- LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 description 1
- 241000283086 Equidae Species 0.000 description 1
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- 102000016359 Fibronectins Human genes 0.000 description 1
- 108010067306 Fibronectins Proteins 0.000 description 1
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 description 1
- 241001494479 Pecora Species 0.000 description 1
- 229920002594 Polyethylene Glycol 8000 Polymers 0.000 description 1
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- AOBORMOPSGHCAX-UHFFFAOYSA-N Tocophersolan Chemical compound OCCOC(=O)CCC(=O)OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C AOBORMOPSGHCAX-UHFFFAOYSA-N 0.000 description 1
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- OGBUMNBNEWYMNJ-UHFFFAOYSA-N batilol Chemical group CCCCCCCCCCCCCCCCCCOCC(O)CO OGBUMNBNEWYMNJ-UHFFFAOYSA-N 0.000 description 1
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- GHVNFZFCNZKVNT-UHFFFAOYSA-M decanoate Chemical compound CCCCCCCCCC([O-])=O GHVNFZFCNZKVNT-UHFFFAOYSA-M 0.000 description 1
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical group CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 description 1
- 229940093471 ethyl oleate Drugs 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
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- 229960002446 octanoic acid Drugs 0.000 description 1
- 230000006320 pegylation Effects 0.000 description 1
- WTJKGGKOPKCXLL-RRHRGVEJSA-N phosphatidylcholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCCCCCCCC WTJKGGKOPKCXLL-RRHRGVEJSA-N 0.000 description 1
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- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/10—Dispersions; Emulsions
- A61K9/107—Emulsions ; Emulsion preconcentrates; Micelles
-
- 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
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A61K31/5375—1,4-Oxazines, e.g. morpholine
- A61K31/5377—1,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- 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]
-
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Dispersion Chemistry (AREA)
- Rheumatology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Immunology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Pain & Pain Management (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US35969410P | 2010-06-29 | 2010-06-29 | |
| US61/359,694 | 2010-06-29 | ||
| PCT/US2011/042162 WO2012006081A1 (en) | 2010-06-29 | 2011-06-28 | Oral formulation of kinase inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2013529686A JP2013529686A (ja) | 2013-07-22 |
| JP2013529686A5 JP2013529686A5 (OSRAM) | 2014-08-14 |
| JP5936609B2 true JP5936609B2 (ja) | 2016-06-22 |
Family
ID=45441513
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013518572A Expired - Fee Related JP5936609B2 (ja) | 2010-06-29 | 2011-06-28 | キナーゼインヒビターの経口製剤 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US9375402B2 (OSRAM) |
| EP (1) | EP2588081A4 (OSRAM) |
| JP (1) | JP5936609B2 (OSRAM) |
| CN (1) | CN103313697B (OSRAM) |
| AU (1) | AU2011276552B2 (OSRAM) |
| CA (1) | CA2803004A1 (OSRAM) |
| MX (1) | MX340819B (OSRAM) |
| NZ (1) | NZ604583A (OSRAM) |
| WO (1) | WO2012006081A1 (OSRAM) |
| ZA (1) | ZA201300009B (OSRAM) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2012216894B2 (en) | 2011-02-17 | 2016-07-14 | Cancer Therapeutics Crc Pty Limited | Selective FAK inhibitors |
| US20130324532A1 (en) | 2011-02-17 | 2013-12-05 | Cancer Therapeutics Crc Pty Limited | Fak inhibitors |
| CN104427976B (zh) | 2012-05-10 | 2018-04-24 | 佩因拉佛姆有限公司 | 疏水的活性成分的储库制剂及其制备方法 |
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| US4656182A (en) | 1983-12-06 | 1987-04-07 | Warner-Lambert Company | Substituted trans-1,2-diaminocyclohexyl amide compounds |
| US20040006005A1 (en) * | 2002-07-02 | 2004-01-08 | Sanjay Bhanot | Use of integrin-linked kinase inhibitors for treating insulin resistance, hyperglycemia and diabetes |
| GB9828511D0 (en) | 1998-12-24 | 1999-02-17 | Zeneca Ltd | Chemical compounds |
| GB0004887D0 (en) | 2000-03-01 | 2000-04-19 | Astrazeneca Uk Ltd | Chemical compounds |
| DE60137069D1 (de) * | 2000-10-11 | 2009-01-29 | Cephalon Inc | Arzneizusammensetzungen enthaltend modafinilverbindungen |
| AR040456A1 (es) | 2002-06-27 | 2005-04-06 | Bristol Myers Squibb Co | Piridina n-oxidos 2,4 -disubstituidos utiles como inhibidores de transcriptasa inversa del virus de inmunodeficiencia humana |
| US20080119515A1 (en) * | 2003-03-10 | 2008-05-22 | M Arshad Siddiqui | Heterocyclic Kinase Inhibitors: Methods of Use and Synthesis |
| GT200500310A (es) * | 2004-11-19 | 2006-06-19 | Compuestos organicos | |
| JP5247154B2 (ja) | 2005-02-18 | 2013-07-24 | テイボテク・フアーマシユーチカルズ | Ｈｉｖ阻害性２−（４−シアノフェニルアミノ）ピリミジンオキシド誘導体 |
| US20070104780A1 (en) * | 2005-10-25 | 2007-05-10 | Lipari John M | Formulation comprising a drug of low water solubility and method of use thereof |
| EP2012753A2 (en) | 2006-04-28 | 2009-01-14 | Schering Corporation | Process for the precipitation and isolation of 6,6-dimethyl-3-aza-bicyclo [3.1.0]hexane-amide compounds by controlled precipitation and pharmaceutical formulations containing same |
| KR20090033904A (ko) | 2006-07-21 | 2009-04-06 | 노파르티스 아게 | 벤즈이미다졸릴 피리딜 에테르의 제제 |
| CA2681015C (en) * | 2007-03-16 | 2016-06-21 | The Scripps Research Institute | Inhibitors of focal adhesion kinase |
| US20090203709A1 (en) * | 2008-02-07 | 2009-08-13 | Abbott Laboratories | Pharmaceutical Dosage Form For Oral Administration Of Tyrosine Kinase Inhibitor |
| US20100317663A1 (en) | 2008-02-19 | 2010-12-16 | Jerry Leroy Adams | Anilinopyridines as inhibitors of fak |
| JP5551689B2 (ja) | 2008-06-17 | 2014-07-16 | アストラゼネカ アクチボラグ | ピリジン化合物 |
| WO2011019943A1 (en) | 2009-08-12 | 2011-02-17 | Poniard Pharmaceuticals, Inc. | Method of promoting apoptosis and inhibiting metastasis |
| WO2011133668A2 (en) | 2010-04-20 | 2011-10-27 | President And Fellows Of Harvard College | Methods and compositions for the treatment of cancer |
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| NZ604583A (en) | 2015-04-24 |
| JP2013529686A (ja) | 2013-07-22 |
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| CN103313697A (zh) | 2013-09-18 |
| US20140206692A1 (en) | 2014-07-24 |
| EP2588081A1 (en) | 2013-05-08 |
| US9375402B2 (en) | 2016-06-28 |
| AU2011276552A1 (en) | 2013-01-10 |
| ZA201300009B (en) | 2013-09-25 |
| CN103313697B (zh) | 2016-06-01 |
| EP2588081A4 (en) | 2014-12-10 |
| MX340819B (es) | 2016-07-26 |
| MX2012014982A (es) | 2013-07-03 |
| AU2011276552B2 (en) | 2015-09-03 |
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