CN102442941A - 用作crth2拮抗剂和抗过敏剂的多环酸化合物 - Google Patents
用作crth2拮抗剂和抗过敏剂的多环酸化合物 Download PDFInfo
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- CN102442941A CN102442941A CN2011102832598A CN201110283259A CN102442941A CN 102442941 A CN102442941 A CN 102442941A CN 2011102832598 A CN2011102832598 A CN 2011102832598A CN 201110283259 A CN201110283259 A CN 201110283259A CN 102442941 A CN102442941 A CN 102442941A
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- Prior art keywords
- esi
- nmr
- phenoxy
- methyl
- propyl group
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 147
- 239000002253 acid Substances 0.000 title description 10
- 239000000043 antiallergic agent Substances 0.000 title description 4
- 125000003367 polycyclic group Chemical group 0.000 title description 3
- 239000005557 antagonist Substances 0.000 title description 2
- 150000003839 salts Chemical class 0.000 claims abstract description 30
- 239000003814 drug Substances 0.000 claims abstract description 9
- 208000006673 asthma Diseases 0.000 claims abstract description 7
- 206010039085 Rhinitis allergic Diseases 0.000 claims abstract description 5
- 201000010105 allergic rhinitis Diseases 0.000 claims abstract description 5
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims abstract description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 255
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 253
- 238000002360 preparation method Methods 0.000 claims description 102
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 88
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 57
- 229910052736 halogen Inorganic materials 0.000 claims description 26
- 150000002367 halogens Chemical class 0.000 claims description 26
- 230000014509 gene expression Effects 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 230000002265 prevention Effects 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims 1
- 201000010099 disease Diseases 0.000 abstract description 9
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 9
- 229940124003 CRTH2 antagonist Drugs 0.000 abstract description 5
- 206010012434 Dermatitis allergic Diseases 0.000 abstract description 3
- 201000008937 atopic dermatitis Diseases 0.000 abstract description 3
- 208000010668 atopic eczema Diseases 0.000 abstract description 3
- 201000009890 sinusitis Diseases 0.000 abstract description 3
- 206010010741 Conjunctivitis Diseases 0.000 abstract description 2
- 208000024780 Urticaria Diseases 0.000 abstract description 2
- 201000006417 multiple sclerosis Diseases 0.000 abstract description 2
- 206010065563 Eosinophilic bronchitis Diseases 0.000 abstract 1
- 208000004262 Food Hypersensitivity Diseases 0.000 abstract 1
- 206010016946 Food allergy Diseases 0.000 abstract 1
- 208000026935 allergic disease Diseases 0.000 abstract 1
- 210000003979 eosinophil Anatomy 0.000 abstract 1
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- 238000005160 1H NMR spectroscopy Methods 0.000 description 433
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- 239000000203 mixture Substances 0.000 description 181
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- 239000002585 base Substances 0.000 description 164
- -1 Prostaglandins Leukotrienes Chemical class 0.000 description 155
- 235000019439 ethyl acetate Nutrition 0.000 description 147
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- OBNCKNCVKJNDBV-UHFFFAOYSA-N ethyl butyrate Chemical compound CCCC(=O)OCC OBNCKNCVKJNDBV-UHFFFAOYSA-N 0.000 description 76
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 73
- 239000011541 reaction mixture Substances 0.000 description 73
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- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 71
- 238000010898 silica gel chromatography Methods 0.000 description 65
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 64
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 64
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 62
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 62
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 62
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- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 55
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- 239000001301 oxygen Substances 0.000 description 55
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- 238000003756 stirring Methods 0.000 description 48
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 44
- 229940017219 methyl propionate Drugs 0.000 description 44
- RJUFJBKOKNCXHH-UHFFFAOYSA-N Methyl propionate Chemical compound CCC(=O)OC RJUFJBKOKNCXHH-UHFFFAOYSA-N 0.000 description 41
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 41
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 39
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 35
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- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 31
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- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 31
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
- 238000006243 chemical reaction Methods 0.000 description 30
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 28
- 239000000284 extract Substances 0.000 description 28
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 27
- 235000002639 sodium chloride Nutrition 0.000 description 27
- 229920006395 saturated elastomer Polymers 0.000 description 25
- 238000000034 method Methods 0.000 description 24
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 23
- 239000007787 solid Substances 0.000 description 23
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- WJJMNDUMQPNECX-UHFFFAOYSA-N dipicolinic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=N1 WJJMNDUMQPNECX-UHFFFAOYSA-N 0.000 description 22
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 21
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 21
- 239000011630 iodine Substances 0.000 description 20
- 229910052740 iodine Inorganic materials 0.000 description 20
- 239000012266 salt solution Substances 0.000 description 20
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 19
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 19
- QDKWLJJOYIFEBS-UHFFFAOYSA-N 1-fluoro-4-$l^{1}-oxidanylbenzene Chemical group [O]C1=CC=C(F)C=C1 QDKWLJJOYIFEBS-UHFFFAOYSA-N 0.000 description 18
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
- 229910052799 carbon Inorganic materials 0.000 description 17
- 238000000605 extraction Methods 0.000 description 17
- 125000001072 heteroaryl group Chemical group 0.000 description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 15
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- 125000003118 aryl group Chemical group 0.000 description 12
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
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- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 8
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- 229910000103 lithium hydride Inorganic materials 0.000 description 8
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 8
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical class OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 description 8
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- SIAPCJWMELPYOE-UHFFFAOYSA-N lithium hydride Chemical compound [LiH] SIAPCJWMELPYOE-UHFFFAOYSA-N 0.000 description 7
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 7
- 239000000843 powder Substances 0.000 description 7
- 229910000104 sodium hydride Inorganic materials 0.000 description 7
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- SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 6
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- YDCHPLOFQATIDS-UHFFFAOYSA-N methyl 2-bromoacetate Chemical compound COC(=O)CBr YDCHPLOFQATIDS-UHFFFAOYSA-N 0.000 description 6
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- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 5
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- LJCNRYVRMXRIQR-OLXYHTOASA-L potassium sodium L-tartrate Chemical compound [Na+].[K+].[O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O LJCNRYVRMXRIQR-OLXYHTOASA-L 0.000 description 5
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- 235000011006 sodium potassium tartrate Nutrition 0.000 description 5
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 4
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- HQSFITLRCKIRLE-UHFFFAOYSA-N 1-[(2-methylpropan-2-yl)oxycarbonyl]indole-4-carboxylic acid Chemical compound C1=CC=C2N(C(=O)OC(C)(C)C)C=CC2=C1C(O)=O HQSFITLRCKIRLE-UHFFFAOYSA-N 0.000 description 3
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 3
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Classifications
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- 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
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- 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
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
-
- 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
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
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- Animal Behavior & Ethology (AREA)
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- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
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- Ophthalmology & Optometry (AREA)
- Otolaryngology (AREA)
- Immunology (AREA)
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Indole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Pyridine Compounds (AREA)
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| CN200780046458A Pending CN101636386A (zh) | 2006-12-14 | 2007-12-13 | 用作crth2拮抗剂和抗过敏剂的多环酸化合物 |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105353095A (zh) * | 2015-11-16 | 2016-02-24 | 华南农业大学 | 一种西地那非及其结构类似物的免疫检测方法 |
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2008219166B2 (en) * | 2007-02-16 | 2013-05-16 | Amgen Inc. | Nitrogen-containing heterocyclyl ketones and their use as c-Met inhibitors |
| US8304413B2 (en) | 2008-06-03 | 2012-11-06 | Intermune, Inc. | Compounds and methods for treating inflammatory and fibrotic disorders |
| MX2011012155A (es) | 2009-05-13 | 2012-02-28 | Enanta Pharm Inc | Compuestos macrociclicos como inhibidores del virus de hepatitis c. |
| EP2590944B1 (en) | 2010-07-05 | 2015-09-30 | Actelion Pharmaceuticals Ltd. | 1-phenyl-substituted heterocyclyl derivatives and their use as prostaglandin d2 receptor modulators |
| US9255090B2 (en) | 2011-12-21 | 2016-02-09 | Actelion Pharmaceuticals Ltd. | Heterocyclyl derivatives and their use as prostaglandin D2 receptor modulators |
| MX2014015156A (es) | 2012-06-12 | 2015-08-06 | Abbvie Inc | Derivados de piridinona y piridazinona. |
| US9169270B2 (en) | 2012-07-05 | 2015-10-27 | Actelion Pharmaceuticals Ltd. | 1-phenyl-substituted heterocyclyl derivatives and their use as prostaglandin D2 receptor modulators |
| WO2014047427A2 (en) | 2012-09-21 | 2014-03-27 | Vanderbilt University | Substituted benzofuran, benzothiophene and indole mcl-1 inhibitors |
| AR092742A1 (es) | 2012-10-02 | 2015-04-29 | Intermune Inc | Piridinonas antifibroticas |
| WO2014080290A2 (en) | 2012-11-21 | 2014-05-30 | Rvx Therapeutics Inc. | Cyclic amines as bromodomain inhibitors |
| WO2014080291A2 (en) | 2012-11-21 | 2014-05-30 | Rvx Therapeutics Inc. | Biaryl derivatives as bromodomain inhibitors |
| AU2013365926B9 (en) * | 2012-12-21 | 2019-01-17 | Zenith Epigenetics Ltd. | Novel heterocyclic compounds as bromodomain inhibitors |
| ES2661437T3 (es) | 2013-06-21 | 2018-04-02 | Zenith Epigenetics Corp. | Nuevos compuestos bicíclicos sustituidos como inhibidores de bromodominio |
| SI3010503T1 (sl) | 2013-06-21 | 2020-07-31 | Zenith Epigenetics Ltd. | Novi biciklični inhibitorji bromodomene |
| CN105593224B (zh) | 2013-07-31 | 2021-05-25 | 恒元生物医药科技(苏州)有限公司 | 作为溴结构域抑制剂的新型喹唑啉酮类化合物 |
| US10005728B2 (en) | 2013-08-28 | 2018-06-26 | Vanderbilt University | Substituted indole Mcl-1 inhibitors |
| CA2943815C (en) | 2014-03-27 | 2023-04-04 | Vanderbilt University | Substituted indole mcl-1 inhibitors |
| KR102373700B1 (ko) | 2014-04-02 | 2022-03-11 | 인터뮨, 인크. | 항섬유성 피리디논 |
| US9949965B2 (en) | 2014-10-17 | 2018-04-24 | Vanderbilt University | Tricyclic indole Mcl-1 inhibitors and uses thereof |
| US10710992B2 (en) | 2014-12-01 | 2020-07-14 | Zenith Epigenetics Ltd. | Substituted pyridinones as bromodomain inhibitors |
| EP3227280B1 (en) | 2014-12-01 | 2019-04-24 | Zenith Epigenetics Ltd. | Substituted pyridines as bromodomain inhibitors |
| US10292968B2 (en) | 2014-12-11 | 2019-05-21 | Zenith Epigenetics Ltd. | Substituted heterocycles as bromodomain inhibitors |
| CA2966450A1 (en) | 2014-12-17 | 2016-06-23 | Olesya KHARENKO | Inhibitors of bromodomains |
| WO2017104728A1 (ja) * | 2015-12-16 | 2017-06-22 | 国立大学法人東京大学 | 食物アレルギー治療薬 |
| WO2017126635A1 (ja) * | 2016-01-22 | 2017-07-27 | 武田薬品工業株式会社 | 複素環化合物およびその用途 |
| EP4292662A3 (en) | 2016-03-04 | 2024-02-21 | Vanderbilt University | Substituted indole mcl-1 inhibitors |
| US11608320B2 (en) | 2020-02-02 | 2023-03-21 | Kuwait University | Oxazolidinone hydroxamic acid derivatives |
Family Cites Families (11)
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| JP3245864B2 (ja) | 1994-03-10 | 2002-01-15 | 藤沢薬品工業株式会社 | プロスタグランジンi2アゴニストとしてのナフタレン誘導体 |
| AU3387895A (en) * | 1994-09-10 | 1996-03-27 | Basf Aktiengesellschaft | Phenylacetic acid alkyl esters |
| AU691673B2 (en) | 1994-11-14 | 1998-05-21 | Dow Agrosciences Llc | Pyridazinones and their use as fungicides |
| DE19514568A1 (de) * | 1995-04-20 | 1996-10-24 | Merck Patent Gmbh | Arylalkyl-pyridazinone |
| KR20020014797A (ko) * | 1999-05-17 | 2002-02-25 | 한센 핀 베네드, 안네 제헤르, 웨이콥 마리안느 | 글루카곤 길항제/역 아고니스트 |
| CA2437932A1 (en) * | 2001-02-12 | 2002-09-19 | Merck Patent Gesellschaft Mit Beschraenkter Haftung | Use of type 4 phosphodiesterase inhibitors in myocardial diseases |
| TW200400930A (en) * | 2002-06-26 | 2004-01-16 | Ono Pharmaceutical Co | Therapeutic agent for chronic disease |
| US7820682B2 (en) * | 2002-10-03 | 2010-10-26 | Ono Pharmaceutical Co., Ltd. | LPA receptor antagonist |
| EP2336113A1 (en) | 2004-05-29 | 2011-06-22 | 7TM Pharma A/S | CRTH2 Receptor Ligands for Medical Use |
| DE102005057924A1 (de) | 2005-12-05 | 2007-06-06 | Merck Patent Gmbh | Pyridazinonderivate |
| DE102006037478A1 (de) * | 2006-08-10 | 2008-02-14 | Merck Patent Gmbh | 2-(Heterocyclylbenzyl)-pyridazinonderivate |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105353095A (zh) * | 2015-11-16 | 2016-02-24 | 华南农业大学 | 一种西地那非及其结构类似物的免疫检测方法 |
Also Published As
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| MX2009006312A (es) | 2009-08-07 |
| JP2010513224A (ja) | 2010-04-30 |
| JP5278318B2 (ja) | 2013-09-04 |
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| PL2094662T3 (pl) | 2012-09-28 |
| CA2672601A1 (en) | 2008-06-19 |
| ES2383239T3 (es) | 2012-06-19 |
| PT2094662E (pt) | 2012-07-02 |
| EP2094662A1 (en) | 2009-09-02 |
| AR064346A1 (es) | 2009-04-01 |
| CN101636386A (zh) | 2010-01-27 |
| TW200848036A (en) | 2008-12-16 |
| ATE553084T1 (de) | 2012-04-15 |
| WO2008072784A1 (en) | 2008-06-19 |
| US8273745B2 (en) | 2012-09-25 |
| KR20090096690A (ko) | 2009-09-14 |
| EP2094662B1 (en) | 2012-04-11 |
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