TWI433672B - 吲唑化合物 - Google Patents
吲唑化合物 Download PDFInfo
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- TWI433672B TWI433672B TW096146086A TW96146086A TWI433672B TW I433672 B TWI433672 B TW I433672B TW 096146086 A TW096146086 A TW 096146086A TW 96146086 A TW96146086 A TW 96146086A TW I433672 B TWI433672 B TW I433672B
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- 125000003453 indazolyl group Chemical class N1N=C(C2=C1C=CC=C2)* 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 34
- 206010028980 Neoplasm Diseases 0.000 claims description 21
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 201000011510 cancer Diseases 0.000 claims description 12
- 229910052799 carbon Inorganic materials 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 40
- -1 carbazole compound Chemical class 0.000 description 27
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 22
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- 125000003118 aryl group Chemical group 0.000 description 17
- 150000001716 carbazoles Chemical class 0.000 description 16
- UJOBWOGCFQCDNV-UHFFFAOYSA-N Carbazole Natural products C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- 125000001072 heteroaryl group Chemical group 0.000 description 14
- 238000000034 method Methods 0.000 description 14
- 210000004027 cell Anatomy 0.000 description 13
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 12
- 239000000243 solution Substances 0.000 description 11
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- 201000010099 disease Diseases 0.000 description 9
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 9
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 9
- 150000002148 esters Chemical class 0.000 description 9
- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 8
- 239000002953 phosphate buffered saline Substances 0.000 description 8
- 206010027476 Metastases Diseases 0.000 description 7
- 125000000392 cycloalkenyl group Chemical group 0.000 description 7
- 125000004366 heterocycloalkenyl group Chemical group 0.000 description 7
- 238000002347 injection Methods 0.000 description 7
- 239000007924 injection Substances 0.000 description 7
- 230000009401 metastasis Effects 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
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- 108010073923 Vascular Endothelial Growth Factor C Proteins 0.000 description 6
- 108010053100 Vascular Endothelial Growth Factor Receptor-3 Proteins 0.000 description 6
- 102000016663 Vascular Endothelial Growth Factor Receptor-3 Human genes 0.000 description 6
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 6
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- 229940125904 compound 1 Drugs 0.000 description 5
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- 229910052757 nitrogen Inorganic materials 0.000 description 5
- DCWXELXMIBXGTH-UHFFFAOYSA-N phosphotyrosine Chemical compound OC(=O)C(N)CC1=CC=C(OP(O)(O)=O)C=C1 DCWXELXMIBXGTH-UHFFFAOYSA-N 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 101000851030 Homo sapiens Vascular endothelial growth factor receptor 3 Proteins 0.000 description 4
- 102100033179 Vascular endothelial growth factor receptor 3 Human genes 0.000 description 4
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- 230000000694 effects Effects 0.000 description 4
- 230000035168 lymphangiogenesis Effects 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- OXWGJOGAZFVLEG-UHFFFAOYSA-N methyl 4-[(3,3-diphenylpropylamino)methyl]-3-nitrobenzoate Chemical compound [O-][N+](=O)C1=CC(C(=O)OC)=CC=C1CNCCC(C=1C=CC=CC=1)C1=CC=CC=C1 OXWGJOGAZFVLEG-UHFFFAOYSA-N 0.000 description 4
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- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 3
- KISZTEOELCMZPY-UHFFFAOYSA-N 3,3-diphenylpropylamine Chemical compound C=1C=CC=CC=1C(CCN)C1=CC=CC=C1 KISZTEOELCMZPY-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- 125000005865 C2-C10alkynyl group Chemical group 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- LNUFLCYMSVYYNW-ZPJMAFJPSA-N [(2r,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[[(3s,5s,8r,9s,10s,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-3-yl]oxy]-4,5-disulfo Chemical compound O([C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1C[C@@H]2CC[C@H]3[C@@H]4CC[C@@H]([C@]4(CC[C@@H]3[C@@]2(C)CC1)C)[C@H](C)CCCC(C)C)[C@H]1O[C@H](COS(O)(=O)=O)[C@@H](OS(O)(=O)=O)[C@H](OS(O)(=O)=O)[C@H]1OS(O)(=O)=O LNUFLCYMSVYYNW-ZPJMAFJPSA-N 0.000 description 3
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- 125000003342 alkenyl group Chemical group 0.000 description 3
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- 238000004458 analytical method Methods 0.000 description 3
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- 229940125773 compound 10 Drugs 0.000 description 3
- 229940125797 compound 12 Drugs 0.000 description 3
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- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 3
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- 150000002367 halogens Chemical class 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 3
- 239000011159 matrix material Substances 0.000 description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 125000006239 protecting group Chemical group 0.000 description 3
- 150000003839 salts Chemical group 0.000 description 3
- 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 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- IWZSHWBGHQBIML-ZGGLMWTQSA-N (3S,8S,10R,13S,14S,17S)-17-isoquinolin-7-yl-N,N,10,13-tetramethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-amine Chemical compound CN(C)[C@H]1CC[C@]2(C)C3CC[C@@]4(C)[C@@H](CC[C@@H]4c4ccc5ccncc5c4)[C@@H]3CC=C2C1 IWZSHWBGHQBIML-ZGGLMWTQSA-N 0.000 description 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 2
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- HYGYRBBZOHUETE-UHFFFAOYSA-N methyl 4-(bromomethyl)-3-nitrobenzoate Chemical compound COC(=O)C1=CC=C(CBr)C([N+]([O-])=O)=C1 HYGYRBBZOHUETE-UHFFFAOYSA-N 0.000 description 2
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- VJOFNWDVXXUHAG-UHFFFAOYSA-N n,n-dimethyl-1-pyridin-4-ylmethanamine Chemical compound CN(C)CC1=CC=NC=C1 VJOFNWDVXXUHAG-UHFFFAOYSA-N 0.000 description 2
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- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 229940100691 oral capsule Drugs 0.000 description 1
- 150000002916 oxazoles Chemical class 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- BMMGVYCKOGBVEV-UHFFFAOYSA-N oxo(oxoceriooxy)cerium Chemical compound [Ce]=O.O=[Ce]=O BMMGVYCKOGBVEV-UHFFFAOYSA-N 0.000 description 1
- 229940124531 pharmaceutical excipient Drugs 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
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- 229920000136 polysorbate Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
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- 239000003755 preservative agent Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
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- 238000004445 quantitative analysis Methods 0.000 description 1
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- 229940051201 quinoline yellow Drugs 0.000 description 1
- FZUOVNMHEAPVBW-UHFFFAOYSA-L quinoline yellow ws Chemical compound [Na+].[Na+].O=C1C2=CC=CC=C2C(=O)C1C1=NC2=C(S([O-])(=O)=O)C=C(S(=O)(=O)[O-])C=C2C=C1 FZUOVNMHEAPVBW-UHFFFAOYSA-L 0.000 description 1
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- 239000012258 stirred mixture Substances 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
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Classifications
-
- 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
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/54—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings condensed with carbocyclic rings or ring systems
- C07D231/56—Benzopyrazoles; Hydrogenated benzopyrazoles
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
-
- 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
-
- 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
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Epidemiology (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US87304106P | 2006-12-05 | 2006-12-05 | |
| US11/949,070 US7825261B2 (en) | 2006-12-05 | 2007-12-03 | Indazole compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW200836720A TW200836720A (en) | 2008-09-16 |
| TWI433672B true TWI433672B (zh) | 2014-04-11 |
Family
ID=39492604
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW096146086A TWI433672B (zh) | 2006-12-05 | 2007-12-04 | 吲唑化合物 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US7825261B2 (https=) |
| EP (1) | EP2091329A4 (https=) |
| JP (1) | JP2010511721A (https=) |
| KR (1) | KR20090127867A (https=) |
| CN (1) | CN101616587A (https=) |
| AU (1) | AU2007329480A1 (https=) |
| CA (1) | CA2671543A1 (https=) |
| TW (1) | TWI433672B (https=) |
| WO (1) | WO2008070599A1 (https=) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR074199A1 (es) | 2008-11-20 | 2010-12-29 | Glaxosmithkline Llc | Compuesto de 6-(4-pirimidinil)-1h-indazol, composiciones farmaceuticas que lo comprenden y su uso para preparar un medicamento util para el tratamiento o disminucion de la gravedad del cancer. |
| DE102009049662A1 (de) | 2009-10-13 | 2011-04-14 | Bayer Schering Pharma Aktiengesellschaft | 2,5-Disubstituierte 2H-Indazole als EP2-Rezeptor-Antagonisten |
| WO2011074658A1 (ja) | 2009-12-18 | 2011-06-23 | 田辺三菱製薬株式会社 | 新規抗血小板薬 |
| JP2013520502A (ja) | 2010-02-25 | 2013-06-06 | メルク・シャープ・エンド・ドーム・コーポレイション | 有用な抗糖尿病薬である新規な環状ベンズイミダゾール誘導体 |
| TW201326154A (zh) | 2011-11-28 | 2013-07-01 | 拜耳知識產權公司 | 作為ｅｐ２受體拮抗劑之新穎２ｈ－吲唑 |
| US8889730B2 (en) | 2012-04-10 | 2014-11-18 | Pfizer Inc. | Indole and indazole compounds that activate AMPK |
| EP2970177A1 (en) | 2013-03-15 | 2016-01-20 | Pfizer Inc. | Indole compounds that activate ampk |
| EP2999469A1 (de) | 2013-05-23 | 2016-03-30 | Bayer Pharma Aktiengesellschaft | Pharmazeutische zusammensetzung und deren verwendung sowie anwendungsregime dieser pharmazeutischen zusammensetzung zur bedarfsweisen ( on-demand") kontrazeption |
| US9199963B2 (en) | 2013-07-09 | 2015-12-01 | Takeda Pharmaceutical Company Limited | Heterocyclic compound |
| KR101713303B1 (ko) | 2015-12-24 | 2017-03-07 | 강원대학교산학협력단 | 2ｈ-인다졸 유도체의 제조방법 |
| GB201617630D0 (en) | 2016-10-18 | 2016-11-30 | Cellcentric Ltd | Pharmaceutical compounds |
| TWI877770B (zh) | 2018-02-27 | 2025-03-21 | 美商英塞特公司 | 作為a2a / a2b抑制劑之咪唑并嘧啶及三唑并嘧啶 |
| GB201806320D0 (en) | 2018-04-18 | 2018-05-30 | Cellcentric Ltd | Process |
| EP3810610A1 (en) | 2018-05-18 | 2021-04-28 | Incyte Corporation | Fused pyrimidine derivatives as a2a / a2b inhibitors |
| WO2020010197A1 (en) | 2018-07-05 | 2020-01-09 | Incyte Corporation | Fused pyrazine derivatives as a2a / a2b inhibitors |
| MX2021003904A (es) | 2018-10-05 | 2021-10-26 | Annapurna Bio Inc | Compuestos y composiciones para el tratamiento de afecciones asociadas con la actividad del receptor apj. |
| US12522583B2 (en) | 2018-11-07 | 2026-01-13 | Dana-Farber Cancer Institute, Inc. | Benzimidazole derivatives and aza-benzimidazole derivatives as Janus kinase 2 inhibitors and uses thereof |
| EP3877371A4 (en) | 2018-11-07 | 2022-07-27 | Dana-Farber Cancer Institute, Inc. | IMIDAZOPYRIDINE DERIVATIVES AND AZA-IMIDAZOPYRIDINE DERIVATIVES AS JANUS KINASE 2 INHIBITORS AND USES THEREOF |
| EP3876939A4 (en) | 2018-11-07 | 2022-08-10 | Dana-Farber Cancer Institute, Inc. | Benzothiazole derivatives and 7-aza-benzothiazole derivatives as janus kinase 2 inhibitors and uses thereof |
| TWI829857B (zh) | 2019-01-29 | 2024-01-21 | 美商英塞特公司 | 作為a2a / a2b抑制劑之吡唑并吡啶及三唑并吡啶 |
| AU2020357941A1 (en) * | 2019-10-01 | 2022-04-28 | Memorial Sloan Kettering Cancer Center | Small molecule inhibitors of Id proteins |
| US11691963B2 (en) | 2020-05-06 | 2023-07-04 | Ajax Therapeutics, Inc. | 6-heteroaryloxy benzimidazoles and azabenzimidazoles as JAK2 inhibitors |
| US12043632B2 (en) | 2020-12-23 | 2024-07-23 | Ajax Therapeutics, Inc. | 6-heteroaryloxy benzimidazoles and azabenzimidazoles as JAK2 inhibitors |
| US12162881B2 (en) | 2021-11-09 | 2024-12-10 | Ajax Therapeutics, Inc. | Forms and compositions of inhibitors of JAK2 |
| WO2023086319A1 (en) | 2021-11-09 | 2023-05-19 | Ajax Therapeutics, Inc. | 6-he tero aryloxy benzimidazoles and azabenzimidazoles as jak2 inhibitors |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EA002113B1 (ru) * | 1996-09-04 | 2001-12-24 | Пфайзер Инк. | Производные индазола и их использование в качестве ингибиторов фосфодиэстеразы (фдэ) типа iv и продуцирования фактора некроза опухоли (фно) |
| WO2000038677A1 (en) * | 1998-12-23 | 2000-07-06 | Allelix Biopharmaceuticals Inc. | Indole and indolizidine derivatives for the treatment of migraine |
| US7141581B2 (en) * | 1999-07-02 | 2006-11-28 | Agouron Pharmaceuticals, Inc. | Indazole compounds and pharmaceutical compositions for inhibiting protein kinases, and methods for their use |
| WO2003020698A2 (en) * | 2001-09-06 | 2003-03-13 | Prochon Biotech Ltd. | Protein tyrosine kinase inhibitors |
| AU2003293376A1 (en) * | 2002-12-10 | 2004-06-30 | Imclone Systems Incorporated | Anti-angiogenic compounds and their use in cancer treatment |
| BRPI0409241A (pt) * | 2003-04-10 | 2006-03-28 | Pfizer | compostos bicìclicos como antagonistas do receptor de nr2b, composições farmacêuticas compreendendo os mesmos e seu uso |
| EP1631568A1 (en) * | 2003-04-18 | 2006-03-08 | Memory Pharmaceuticals Corporation | Pyrazole derivatives as phosphodiesterase 4 inhibitors |
| JP2007532658A (ja) * | 2004-04-16 | 2007-11-15 | スミスクライン ビーチャム コーポレーション | がんの治療方法 |
| EP1799673A1 (en) * | 2004-10-15 | 2007-06-27 | Memory Pharmaceuticals Corporation | Pyrazole derivatives as phosphodiesterase 4 inhibitors |
| MX2007007797A (es) * | 2004-12-27 | 2007-08-23 | Alcon Inc | Analogo de aminopirazina para tratar glaucoma y otras enfermedades mediadas por rho cinasa. |
| JP5116687B2 (ja) * | 2005-11-02 | 2013-01-09 | バイエル・ファルマ・アクチェンゲゼルシャフト | がんおよび他の過剰増殖性疾患の処置のためのピロロ［２，１−ｆ］［１，２，４］トリアジン−４−イルアミンＩＧＦ−１Ｒキナーゼ阻害剤 |
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2007
- 2007-12-03 US US11/949,070 patent/US7825261B2/en not_active Expired - Fee Related
- 2007-12-03 CA CA002671543A patent/CA2671543A1/en not_active Abandoned
- 2007-12-03 KR KR1020097014013A patent/KR20090127867A/ko not_active Withdrawn
- 2007-12-03 CN CN200780045197A patent/CN101616587A/zh active Pending
- 2007-12-03 JP JP2009540401A patent/JP2010511721A/ja not_active Withdrawn
- 2007-12-03 EP EP07865081A patent/EP2091329A4/en not_active Withdrawn
- 2007-12-03 WO PCT/US2007/086220 patent/WO2008070599A1/en not_active Ceased
- 2007-12-03 AU AU2007329480A patent/AU2007329480A1/en not_active Abandoned
- 2007-12-04 TW TW096146086A patent/TWI433672B/zh not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| US7825261B2 (en) | 2010-11-02 |
| JP2010511721A (ja) | 2010-04-15 |
| KR20090127867A (ko) | 2009-12-14 |
| CA2671543A1 (en) | 2008-06-12 |
| AU2007329480A1 (en) | 2008-06-12 |
| US20080132501A1 (en) | 2008-06-05 |
| EP2091329A1 (en) | 2009-08-26 |
| EP2091329A4 (en) | 2011-02-23 |
| TW200836720A (en) | 2008-09-16 |
| WO2008070599A1 (en) | 2008-06-12 |
| CN101616587A (zh) | 2009-12-30 |
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