CA2723798A1 - Therapeutically useful substituted hydropyrido [3,2,1-ij] quinoline compounds - Google Patents
Therapeutically useful substituted hydropyrido [3,2,1-ij] quinoline compounds Download PDFInfo
- Publication number
- CA2723798A1 CA2723798A1 CA2723798A CA2723798A CA2723798A1 CA 2723798 A1 CA2723798 A1 CA 2723798A1 CA 2723798 A CA2723798 A CA 2723798A CA 2723798 A CA2723798 A CA 2723798A CA 2723798 A1 CA2723798 A1 CA 2723798A1
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- group
- hydroxyalkyl
- hydrocarbyl
- hydrogen
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 125000002943 quinolinyl group Chemical class N1=C(C=CC2=CC=CC=C12)* 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 67
- 239000003814 drug Substances 0.000 claims abstract description 6
- -1 halohydrocarbyl Chemical group 0.000 claims description 149
- 229910052739 hydrogen Inorganic materials 0.000 claims description 70
- 239000001257 hydrogen Substances 0.000 claims description 69
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 68
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 63
- 125000003118 aryl group Chemical group 0.000 claims description 62
- 150000002431 hydrogen Chemical class 0.000 claims description 55
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 54
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 54
- 125000003545 alkoxy group Chemical group 0.000 claims description 51
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 51
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 51
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 51
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 50
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims description 50
- 125000003282 alkyl amino group Chemical group 0.000 claims description 47
- 125000005157 alkyl carboxy group Chemical group 0.000 claims description 42
- 125000005243 carbonyl alkyl group Chemical group 0.000 claims description 29
- 239000007787 solid Substances 0.000 claims description 23
- 125000001475 halogen functional group Chemical group 0.000 claims description 22
- 125000003342 alkenyl group Chemical group 0.000 claims description 21
- 125000000304 alkynyl group Chemical group 0.000 claims description 21
- 150000003839 salts Chemical class 0.000 claims description 21
- 229910052760 oxygen Inorganic materials 0.000 claims description 19
- 229940002612 prodrug Drugs 0.000 claims description 16
- 239000000651 prodrug Substances 0.000 claims description 16
- 229910052799 carbon Inorganic materials 0.000 claims description 15
- 125000001424 substituent group Chemical group 0.000 claims description 15
- 229910052717 sulfur Inorganic materials 0.000 claims description 15
- 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 13
- 125000004122 cyclic group Chemical group 0.000 claims description 13
- 125000001072 heteroaryl group Chemical group 0.000 claims description 13
- 125000000623 heterocyclic group Chemical group 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- 125000005599 alkyl carboxylate group Chemical group 0.000 claims description 12
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 12
- 150000004677 hydrates Chemical class 0.000 claims description 12
- 239000012453 solvate Substances 0.000 claims description 12
- 208000002193 Pain Diseases 0.000 claims description 11
- 230000036407 pain Effects 0.000 claims description 11
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 10
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 125000004043 oxo group Chemical group O=* 0.000 claims description 9
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
- 239000001301 oxygen Substances 0.000 claims description 7
- 241000124008 Mammalia Species 0.000 claims description 6
- 150000001412 amines Chemical group 0.000 claims description 6
- 201000010099 disease Diseases 0.000 claims description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- DUYSYHSSBDVJSM-KRWOKUGFSA-N sphingosine 1-phosphate Chemical compound CCCCCCCCCCCCC\C=C\[C@@H](O)[C@@H](N)COP(O)(O)=O DUYSYHSSBDVJSM-KRWOKUGFSA-N 0.000 claims description 6
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 5
- 241000282414 Homo sapiens Species 0.000 claims description 5
- 206010012689 Diabetic retinopathy Diseases 0.000 claims description 4
- 206010061323 Optic neuropathy Diseases 0.000 claims description 4
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- 208000003556 Dry Eye Syndromes Diseases 0.000 claims description 3
- 206010013774 Dry eye Diseases 0.000 claims description 3
- 208000010412 Glaucoma Diseases 0.000 claims description 3
- XOCUXOWLYLLJLV-UHFFFAOYSA-N [O].[S] Chemical compound [O].[S] XOCUXOWLYLLJLV-UHFFFAOYSA-N 0.000 claims description 3
- 230000033115 angiogenesis Effects 0.000 claims description 3
- 230000004406 elevated intraocular pressure Effects 0.000 claims description 3
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims description 2
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- 208000008035 Back Pain Diseases 0.000 claims description 2
- 206010058019 Cancer Pain Diseases 0.000 claims description 2
- 206010007559 Cardiac failure congestive Diseases 0.000 claims description 2
- 208000005590 Choroidal Neovascularization Diseases 0.000 claims description 2
- 206010060823 Choroidal neovascularisation Diseases 0.000 claims description 2
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 2
- 208000032131 Diabetic Neuropathies Diseases 0.000 claims description 2
- 206010019233 Headaches Diseases 0.000 claims description 2
- 206010019280 Heart failures Diseases 0.000 claims description 2
- 208000033463 Ischaemic neuropathy Diseases 0.000 claims description 2
- 208000004852 Lung Injury Diseases 0.000 claims description 2
- 208000019695 Migraine disease Diseases 0.000 claims description 2
- 208000000112 Myalgia Diseases 0.000 claims description 2
- 201000010183 Papilledema Diseases 0.000 claims description 2
- 208000013616 Respiratory Distress Syndrome Diseases 0.000 claims description 2
- 208000017442 Retinal disease Diseases 0.000 claims description 2
- 206010038886 Retinal oedema Diseases 0.000 claims description 2
- 206010038923 Retinopathy Diseases 0.000 claims description 2
- 206010038933 Retinopathy of prematurity Diseases 0.000 claims description 2
- 206010072170 Skin wound Diseases 0.000 claims description 2
- 206010069363 Traumatic lung injury Diseases 0.000 claims description 2
- 206010069351 acute lung injury Diseases 0.000 claims description 2
- 201000000028 adult respiratory distress syndrome Diseases 0.000 claims description 2
- 206010003119 arrhythmia Diseases 0.000 claims description 2
- 208000006673 asthma Diseases 0.000 claims description 2
- 208000006218 bradycardia Diseases 0.000 claims description 2
- 230000036471 bradycardia Effects 0.000 claims description 2
- 239000002537 cosmetic Substances 0.000 claims description 2
- 230000003412 degenerative effect Effects 0.000 claims description 2
- 231100000869 headache Toxicity 0.000 claims description 2
- 230000035876 healing Effects 0.000 claims description 2
- 208000002551 irritable bowel syndrome Diseases 0.000 claims description 2
- 231100000515 lung injury Toxicity 0.000 claims description 2
- 208000002780 macular degeneration Diseases 0.000 claims description 2
- 206010027599 migraine Diseases 0.000 claims description 2
- 208000013465 muscle pain Diseases 0.000 claims description 2
- 201000011195 retinal edema Diseases 0.000 claims description 2
- 230000002207 retinal effect Effects 0.000 claims description 2
- 238000009423 ventilation Methods 0.000 claims description 2
- 208000009935 visceral pain Diseases 0.000 claims description 2
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 1
- 230000001404 mediated effect Effects 0.000 claims 1
- 208000005069 pulmonary fibrosis Diseases 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 19
- 238000002560 therapeutic procedure Methods 0.000 abstract 1
- 238000005481 NMR spectroscopy Methods 0.000 description 49
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 38
- CSCPPACGZOOCGX-WFGJKAKNSA-N acetone d6 Chemical compound [2H]C([2H])([2H])C(=O)C([2H])([2H])[2H] CSCPPACGZOOCGX-WFGJKAKNSA-N 0.000 description 37
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 36
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 30
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 28
- 239000000543 intermediate Substances 0.000 description 28
- 125000005843 halogen group Chemical group 0.000 description 27
- 239000000460 chlorine Substances 0.000 description 26
- 229910052801 chlorine Inorganic materials 0.000 description 24
- 238000003820 Medium-pressure liquid chromatography Methods 0.000 description 23
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 22
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 21
- 238000005160 1H NMR spectroscopy Methods 0.000 description 20
- 101150041968 CDC13 gene Proteins 0.000 description 20
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 20
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 19
- 229910052786 argon Inorganic materials 0.000 description 19
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 18
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 18
- 239000002244 precipitate Substances 0.000 description 17
- 239000000243 solution Substances 0.000 description 16
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 15
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- 125000000524 functional group Chemical group 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 238000002360 preparation method Methods 0.000 description 12
- 235000019439 ethyl acetate Nutrition 0.000 description 11
- 239000000741 silica gel Substances 0.000 description 11
- 229910002027 silica gel Inorganic materials 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- 238000010626 work up procedure Methods 0.000 description 10
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 9
- 229910019142 PO4 Inorganic materials 0.000 description 9
- 239000010452 phosphate Substances 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
- 102000011011 Sphingosine 1-phosphate receptors Human genes 0.000 description 8
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 8
- 108020003175 receptors Proteins 0.000 description 8
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 7
- 108050001083 Sphingosine 1-phosphate receptors Proteins 0.000 description 7
- 239000012634 fragment Substances 0.000 description 7
- 229910052740 iodine Inorganic materials 0.000 description 7
- 102000005962 receptors Human genes 0.000 description 7
- WWUZIQQURGPMPG-UHFFFAOYSA-N (-)-D-erythro-Sphingosine Natural products CCCCCCCCCCCCCC=CC(O)C(N)CO WWUZIQQURGPMPG-UHFFFAOYSA-N 0.000 description 6
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 description 6
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 125000001188 haloalkyl group Chemical group 0.000 description 6
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- WWUZIQQURGPMPG-KRWOKUGFSA-N sphingosine Chemical compound CCCCCCCCCCCCC\C=C\[C@@H](O)[C@@H](N)CO WWUZIQQURGPMPG-KRWOKUGFSA-N 0.000 description 6
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- JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 5
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 5
- 239000012981 Hank's balanced salt solution Substances 0.000 description 5
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical class N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 5
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- VVGIYYKRAMHVLU-UHFFFAOYSA-N newbouldiamide Natural products CCCCCCCCCCCCCCCCCCCC(O)C(O)C(O)C(CO)NC(=O)CCCCCCCCCCCCCCCCC VVGIYYKRAMHVLU-UHFFFAOYSA-N 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
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- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
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Landscapes
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Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US5153308P | 2008-05-08 | 2008-05-08 | |
| US61/051,533 | 2008-05-08 | ||
| US12/433,978 US20090281322A1 (en) | 2008-05-08 | 2009-05-01 | THERAPEUTICALLY USEFUL SUBSTITUTED 1,7-DIPHENYL-1,2,3,5,6,7-HEXAHYDROPYRIDO[3,2,1-Ij]QUINOLINE COMPOUNDS |
| US12/433,978 | 2009-05-01 | ||
| PCT/US2009/043149 WO2009137681A1 (en) | 2008-05-08 | 2009-05-07 | Therapeutically useful substituted hydropyrido [3,2,1-ij] quinoline compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2723798A1 true CA2723798A1 (en) | 2009-11-12 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2723798A Abandoned CA2723798A1 (en) | 2008-05-08 | 2009-05-07 | Therapeutically useful substituted hydropyrido [3,2,1-ij] quinoline compounds |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US20090281322A1 (cg-RX-API-DMAC7.html) |
| EP (1) | EP2294069B1 (cg-RX-API-DMAC7.html) |
| JP (1) | JP5432246B2 (cg-RX-API-DMAC7.html) |
| CN (1) | CN102089306A (cg-RX-API-DMAC7.html) |
| AU (1) | AU2009244199B2 (cg-RX-API-DMAC7.html) |
| BR (1) | BRPI0912534A2 (cg-RX-API-DMAC7.html) |
| CA (1) | CA2723798A1 (cg-RX-API-DMAC7.html) |
| IL (1) | IL209200A0 (cg-RX-API-DMAC7.html) |
| RU (1) | RU2010149312A (cg-RX-API-DMAC7.html) |
| WO (1) | WO2009137681A1 (cg-RX-API-DMAC7.html) |
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| RU2013147049A (ru) * | 2011-03-25 | 2015-04-27 | Аллерган, Инк. | Антагонисты s1p как вспомогательные средства для понижения внутриглазного давления |
| KR101691954B1 (ko) * | 2016-04-26 | 2017-01-02 | 고려대학교 산학협력단 | 신규 n-아실유레아 유도체 및 이를 함유하는 심혈관질환의 예방 또는 치료용 조성물 |
| CN107369775B (zh) * | 2017-07-13 | 2018-12-25 | 长春海谱润斯科技有限公司 | 一种有机电致发光材料及其有机发光器件 |
| CN107492597B (zh) * | 2017-08-10 | 2018-11-27 | 长春海谱润斯科技有限公司 | 一种顶发射有机发光器件 |
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| CA2473740A1 (en) * | 2002-01-18 | 2003-07-31 | David Solow-Cordero | Methods of treating conditions associated with an edg receptor |
| BR0314393A (pt) * | 2002-09-17 | 2005-07-19 | Warner Lambert Co | Piperazinas heterocìclicas substituìdas para o tratamento de esquizofrenia |
| US20040131648A1 (en) * | 2002-10-24 | 2004-07-08 | The Procter & Gamble Company | Nuclear hormone receptor compounds, products and methods employing same |
| US20040167185A1 (en) * | 2003-01-16 | 2004-08-26 | Geetha Shankar | Methods of treating conditions associated with an Edg-3 receptor |
| CA2669736C (en) * | 2005-11-03 | 2017-02-21 | Chembridge Research Laboratories, Inc. | Heterocyclic compounds as tyrosine kinase modulators |
| WO2007112322A2 (en) * | 2006-03-28 | 2007-10-04 | Allergan, Inc. | Indole compounds having sphingosine-1-phosphate (s1p) receptor agonist and/or antagonist biological activity |
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2009
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- 2009-05-07 WO PCT/US2009/043149 patent/WO2009137681A1/en not_active Ceased
- 2009-05-07 EP EP09743667.9A patent/EP2294069B1/en not_active Not-in-force
- 2009-05-07 AU AU2009244199A patent/AU2009244199B2/en not_active Ceased
- 2009-05-07 CA CA2723798A patent/CA2723798A1/en not_active Abandoned
- 2009-05-07 CN CN2009801266353A patent/CN102089306A/zh active Pending
- 2009-05-07 JP JP2011508667A patent/JP5432246B2/ja not_active Expired - Fee Related
-
2010
- 2010-11-08 IL IL209200A patent/IL209200A0/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU2009244199A1 (en) | 2011-10-06 |
| RU2010149312A (ru) | 2012-06-20 |
| JP2011527286A (ja) | 2011-10-27 |
| US20090281322A1 (en) | 2009-11-12 |
| JP5432246B2 (ja) | 2014-03-05 |
| IL209200A0 (en) | 2011-01-31 |
| AU2009244199B2 (en) | 2013-09-19 |
| BRPI0912534A2 (pt) | 2015-10-13 |
| WO2009137681A1 (en) | 2009-11-12 |
| EP2294069A1 (en) | 2011-03-16 |
| CN102089306A (zh) | 2011-06-08 |
| EP2294069B1 (en) | 2015-09-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request |
Effective date: 20140401 |
|
| FZDE | Discontinued |
Effective date: 20160509 |