AU2009244199B2 - 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
- AU2009244199B2 AU2009244199B2 AU2009244199A AU2009244199A AU2009244199B2 AU 2009244199 B2 AU2009244199 B2 AU 2009244199B2 AU 2009244199 A AU2009244199 A AU 2009244199A AU 2009244199 A AU2009244199 A AU 2009244199A AU 2009244199 B2 AU2009244199 B2 AU 2009244199B2
- Authority
- AU
- Australia
- Prior art keywords
- alkyl
- pct
- pain
- compound
- hexahydropyrido
- 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.)
- Ceased
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 62
- 239000003814 drug Substances 0.000 claims abstract description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 54
- 239000001257 hydrogen Substances 0.000 claims description 49
- 229910052801 chlorine Inorganic materials 0.000 claims description 33
- 125000005843 halogen group Chemical group 0.000 claims description 29
- 125000000217 alkyl group Chemical group 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 19
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 18
- 229910052799 carbon Inorganic materials 0.000 claims description 18
- 208000002193 Pain Diseases 0.000 claims description 16
- 230000036407 pain Effects 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 16
- 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 16
- 125000003342 alkenyl group Chemical group 0.000 claims description 13
- 229910052757 nitrogen Inorganic materials 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
- 125000001424 substituent group Chemical group 0.000 claims description 13
- 241000124008 Mammalia Species 0.000 claims description 12
- VFKHECGAEJNAMV-HETMPLHPSA-N (1s,2r,3s,4r)-4-(6-aminopurin-9-yl)cyclopentane-1,2,3-triol Chemical group C1=NC=2C(N)=NC=NC=2N1[C@@H]1C[C@H](O)[C@@H](O)[C@H]1O VFKHECGAEJNAMV-HETMPLHPSA-N 0.000 claims description 11
- 201000010099 disease Diseases 0.000 claims description 10
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 9
- 239000001301 oxygen Substances 0.000 claims description 9
- 229910052717 sulfur Inorganic materials 0.000 claims description 9
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 7
- 229910052794 bromium Inorganic materials 0.000 claims description 7
- 229910052731 fluorine Inorganic materials 0.000 claims description 7
- 239000011593 sulfur Chemical group 0.000 claims description 7
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- 241000282414 Homo sapiens Species 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
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- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 3
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- 201000010183 Papilledema Diseases 0.000 claims description 3
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- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 2
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- 238000004519 manufacturing process Methods 0.000 claims description 2
- 201000000028 adult respiratory distress syndrome Diseases 0.000 claims 2
- 208000005069 pulmonary fibrosis Diseases 0.000 claims 2
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 1
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 1
- 230000000302 ischemic effect Effects 0.000 claims 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims 1
- 201000001119 neuropathy Diseases 0.000 claims 1
- 230000007823 neuropathy Effects 0.000 claims 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 19
- 238000002560 therapeutic procedure Methods 0.000 abstract 1
- -1 halohydrocarbyl Chemical group 0.000 description 81
- 238000005481 NMR spectroscopy Methods 0.000 description 60
- 125000001183 hydrocarbyl group Chemical group 0.000 description 43
- 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
- 125000003118 aryl group Chemical group 0.000 description 36
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 36
- 239000000460 chlorine Substances 0.000 description 35
- 150000002431 hydrogen Chemical class 0.000 description 30
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 30
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 28
- 239000000543 intermediate Substances 0.000 description 28
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 description 27
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 27
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 27
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 27
- 125000003545 alkoxy group Chemical group 0.000 description 26
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 26
- 125000004093 cyano group Chemical group *C#N 0.000 description 26
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 26
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
- 238000003820 Medium-pressure liquid chromatography Methods 0.000 description 23
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 description 23
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 22
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 22
- 125000003282 alkyl amino group Chemical group 0.000 description 22
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 20
- 125000005157 alkyl carboxy group Chemical group 0.000 description 19
- 229910052786 argon Inorganic materials 0.000 description 19
- 239000002244 precipitate Substances 0.000 description 17
- 239000000243 solution Substances 0.000 description 17
- 239000007787 solid 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
- 125000005243 carbonyl alkyl group Chemical group 0.000 description 14
- 210000004027 cell Anatomy 0.000 description 14
- 239000011541 reaction mixture Substances 0.000 description 14
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 13
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical class N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 13
- 125000000524 functional group Chemical group 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 238000002360 preparation method Methods 0.000 description 12
- 125000004122 cyclic group Chemical group 0.000 description 11
- 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
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 10
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 10
- 125000000304 alkynyl group Chemical group 0.000 description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- 238000010626 work up procedure Methods 0.000 description 10
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- 125000001188 haloalkyl group Chemical group 0.000 description 9
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- 238000005160 1H NMR spectroscopy Methods 0.000 description 8
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 8
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- 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 description 6
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- 230000000116 mitigating effect Effects 0.000 description 1
- 230000011278 mitosis Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- SXGURHSLXPDJBC-UHFFFAOYSA-N n-(5-aminopyridin-2-yl)acetamide Chemical compound CC(=O)NC1=CC=C(N)C=N1 SXGURHSLXPDJBC-UHFFFAOYSA-N 0.000 description 1
- CANLDFLYBBBTKC-UHFFFAOYSA-N n-butyl-1,7-diphenyl-1,2,3,5,6,7-hexahydropyrido[3,2,1-ij]quinoline-9-carboxamide Chemical compound C1=2C3=CC(C(=O)NCCCC)=CC=2C(C=2C=CC=CC=2)CCN1CCC3C1=CC=CC=C1 CANLDFLYBBBTKC-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 210000005036 nerve Anatomy 0.000 description 1
- 210000000653 nervous system Anatomy 0.000 description 1
- 230000004770 neurodegeneration Effects 0.000 description 1
- 208000015122 neurodegenerative disease Diseases 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- MONRWRVYLOHUFA-UHFFFAOYSA-N pentylurea Chemical compound CCCCCNC(N)=O MONRWRVYLOHUFA-UHFFFAOYSA-N 0.000 description 1
- 125000005981 pentynyl group Chemical group 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000013641 positive control Substances 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- DBABZHXKTCFAPX-UHFFFAOYSA-N probenecid Chemical compound CCCN(CCC)S(=O)(=O)C1=CC=C(C(O)=O)C=C1 DBABZHXKTCFAPX-UHFFFAOYSA-N 0.000 description 1
- 229960003081 probenecid Drugs 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- 230000002685 pulmonary effect Effects 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 230000027425 release of sequestered calcium ion into cytosol Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 108010035597 sphingosine kinase Proteins 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 230000026683 transduction Effects 0.000 description 1
- 238000010361 transduction Methods 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 230000035899 viability Effects 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
Classifications
-
- 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
- C07D471/02—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 in which the condensed system contains two hetero rings
- C07D471/06—Peri-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P25/04—Centrally acting analgesics, e.g. opioids
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P25/06—Antimigraine agents
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
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- A—HUMAN NECESSITIES
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- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
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- A—HUMAN NECESSITIES
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- A61P9/06—Antiarrhythmics
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- 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
- C07D471/02—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 in which the condensed system contains two hetero rings
- 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
- C07D471/12—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 in which the condensed system contains three hetero rings
- C07D471/16—Peri-condensed systems
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Neurology (AREA)
- Cardiology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Heart & Thoracic Surgery (AREA)
- Ophthalmology & Optometry (AREA)
- Pain & Pain Management (AREA)
- Pulmonology (AREA)
- Diabetes (AREA)
- Rheumatology (AREA)
- Endocrinology (AREA)
- Emergency Medicine (AREA)
- Hospice & Palliative Care (AREA)
- Vascular Medicine (AREA)
- Hematology (AREA)
- Urology & Nephrology (AREA)
- Dermatology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Obesity (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
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 (2)
| Publication Number | Publication Date |
|---|---|
| AU2009244199A1 AU2009244199A1 (en) | 2011-10-06 |
| AU2009244199B2 true AU2009244199B2 (en) | 2013-09-19 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2009244199A Ceased AU2009244199B2 (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 (enExample) |
| EP (1) | EP2294069B1 (enExample) |
| JP (1) | JP5432246B2 (enExample) |
| CN (1) | CN102089306A (enExample) |
| AU (1) | AU2009244199B2 (enExample) |
| BR (1) | BRPI0912534A2 (enExample) |
| CA (1) | CA2723798A1 (enExample) |
| IL (1) | IL209200A0 (enExample) |
| RU (1) | RU2010149312A (enExample) |
| WO (1) | WO2009137681A1 (enExample) |
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| BR112013024657A2 (pt) * | 2011-03-25 | 2016-12-20 | Allergan Inc | antagonistas da s1p como hipotensivos oculares adjuntos |
| 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 |
Citations (1)
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|---|---|---|---|---|
| WO2003062392A2 (en) * | 2002-01-18 | 2003-07-31 | Ceretek Llc | Methods of treating conditions associated with an edg receptor |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| EP1546143A1 (en) * | 2002-09-17 | 2005-06-29 | Warner-Lambert Company LLC | Heterocyclic substituted piperazines for the treatment of schizophrenia |
| 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 |
| US8629147B2 (en) * | 2005-11-03 | 2014-01-14 | Chembridge Corporation | Heterocyclic compounds useful in the treatment of neoplastic diseases, inflammatory disorders and immunomodulatory disorders |
| 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
- 2009-05-01 US US12/433,978 patent/US20090281322A1/en not_active Abandoned
- 2009-05-07 BR BRPI0912534A patent/BRPI0912534A2/pt not_active IP Right Cessation
- 2009-05-07 JP JP2011508667A patent/JP5432246B2/ja not_active Expired - Fee Related
- 2009-05-07 WO PCT/US2009/043149 patent/WO2009137681A1/en not_active Ceased
- 2009-05-07 RU RU2010149312/04A patent/RU2010149312A/ru not_active Application Discontinuation
- 2009-05-07 AU AU2009244199A patent/AU2009244199B2/en not_active Ceased
- 2009-05-07 EP EP09743667.9A patent/EP2294069B1/en not_active Not-in-force
- 2009-05-07 CA CA2723798A patent/CA2723798A1/en not_active Abandoned
- 2009-05-07 CN CN2009801266353A patent/CN102089306A/zh active Pending
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2010
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Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003062392A2 (en) * | 2002-01-18 | 2003-07-31 | Ceretek Llc | Methods of treating conditions associated with an edg receptor |
Also Published As
| Publication number | Publication date |
|---|---|
| US20090281322A1 (en) | 2009-11-12 |
| CA2723798A1 (en) | 2009-11-12 |
| CN102089306A (zh) | 2011-06-08 |
| RU2010149312A (ru) | 2012-06-20 |
| IL209200A0 (en) | 2011-01-31 |
| AU2009244199A1 (en) | 2011-10-06 |
| JP5432246B2 (ja) | 2014-03-05 |
| EP2294069B1 (en) | 2015-09-02 |
| WO2009137681A1 (en) | 2009-11-12 |
| JP2011527286A (ja) | 2011-10-27 |
| EP2294069A1 (en) | 2011-03-16 |
| BRPI0912534A2 (pt) | 2015-10-13 |
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