CN1625393A - 治疗耳鸣的α2δ配体 - Google Patents
治疗耳鸣的α2δ配体 Download PDFInfo
- Publication number
- CN1625393A CN1625393A CNA038031388A CN03803138A CN1625393A CN 1625393 A CN1625393 A CN 1625393A CN A038031388 A CNA038031388 A CN A038031388A CN 03803138 A CN03803138 A CN 03803138A CN 1625393 A CN1625393 A CN 1625393A
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- China
- Prior art keywords
- methyl
- amino methyl
- acid
- amino
- acetic acid
- 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.)
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- 239000003446 ligand Substances 0.000 title claims abstract description 55
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- 231100000886 tinnitus Toxicity 0.000 title claims abstract description 24
- 150000001875 compounds Chemical class 0.000 claims abstract description 288
- 238000000034 method Methods 0.000 claims abstract description 187
- 150000003839 salts Chemical class 0.000 claims abstract description 109
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 59
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 38
- 239000001257 hydrogen Substances 0.000 claims abstract description 37
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 6
- -1 2-amino methyl-4-methyl-amyl Chemical group 0.000 claims description 188
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 162
- 239000002253 acid Substances 0.000 claims description 120
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 27
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 24
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 20
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 20
- 125000000623 heterocyclic group Chemical group 0.000 claims description 15
- 125000003545 alkoxy group Chemical group 0.000 claims description 13
- 230000008569 process Effects 0.000 claims description 13
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- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 150000003009 phosphonic acids Chemical group 0.000 claims description 9
- AYXYPKUFHZROOJ-ZETCQYMHSA-N pregabalin Chemical compound CC(C)C[C@H](CN)CC(O)=O AYXYPKUFHZROOJ-ZETCQYMHSA-N 0.000 claims description 9
- NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical compound C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
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- 229960001233 pregabalin Drugs 0.000 claims description 7
- CWSXPZYRFGYVBO-UHFFFAOYSA-N 4-methyl-2-(2h-tetrazol-5-ylmethyl)pentan-1-amine Chemical compound CC(C)CC(CN)CC1=NN=NN1 CWSXPZYRFGYVBO-UHFFFAOYSA-N 0.000 claims description 6
- 241000124008 Mammalia Species 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 125000002769 thiazolinyl group Chemical group 0.000 claims description 5
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
- QFLSQUNSWXMJBE-UHFFFAOYSA-N [1-(aminomethyl)cyclohexyl]methylphosphonic acid Chemical class OP(=O)(O)CC1(CN)CCCCC1 QFLSQUNSWXMJBE-UHFFFAOYSA-N 0.000 claims description 3
- PBJUNZJWGZTSKL-MRXNPFEDSA-N tiagabine Chemical compound C1=CSC(C(=CCCN2C[C@@H](CCC2)C(O)=O)C2=C(C=CS2)C)=C1C PBJUNZJWGZTSKL-MRXNPFEDSA-N 0.000 claims description 3
- 229960001918 tiagabine Drugs 0.000 claims description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 239000000651 prodrug Substances 0.000 claims description 2
- 229940002612 prodrug Drugs 0.000 claims description 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 2
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- 125000004432 carbon atom Chemical group C* 0.000 claims 16
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical group OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 3
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- 239000000243 solution Substances 0.000 description 343
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 198
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 172
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 154
- 239000000203 mixture Substances 0.000 description 145
- 239000004519 grease Substances 0.000 description 121
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 115
- 235000019439 ethyl acetate Nutrition 0.000 description 113
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 93
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 86
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- 238000005481 NMR spectroscopy Methods 0.000 description 84
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 65
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 63
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- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 62
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- 239000000376 reactant Substances 0.000 description 48
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- 239000000460 chlorine Substances 0.000 description 45
- 239000000284 extract Substances 0.000 description 44
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 43
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- 239000002904 solvent Substances 0.000 description 43
- 208000035126 Facies Diseases 0.000 description 42
- 238000002360 preparation method Methods 0.000 description 42
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 38
- 238000005160 1H NMR spectroscopy Methods 0.000 description 34
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 34
- 239000012141 concentrate Substances 0.000 description 33
- 239000002585 base Substances 0.000 description 32
- 238000004364 calculation method Methods 0.000 description 32
- 229920006395 saturated elastomer Polymers 0.000 description 31
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- 238000003818 flash chromatography Methods 0.000 description 30
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 26
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium on carbon Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 26
- 150000001721 carbon Chemical group 0.000 description 26
- 238000001914 filtration Methods 0.000 description 26
- 239000003921 oil Substances 0.000 description 26
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- 229910000104 sodium hydride Inorganic materials 0.000 description 26
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- 230000002194 synthesizing effect Effects 0.000 description 25
- YOOHANJKYCQHED-UHFFFAOYSA-N 2-[1-[[(2-methylpropan-2-yl)oxycarbonylamino]methyl]cyclohexyl]acetic acid Chemical compound CC(C)(C)OC(=O)NCC1(CC(O)=O)CCCCC1 YOOHANJKYCQHED-UHFFFAOYSA-N 0.000 description 24
- 239000007788 liquid Substances 0.000 description 24
- 238000010992 reflux Methods 0.000 description 24
- 238000011282 treatment Methods 0.000 description 23
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 22
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 22
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- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 20
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- 101150065749 Churc1 gene Proteins 0.000 description 19
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- 229910052786 argon Inorganic materials 0.000 description 19
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 18
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- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 17
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- RAFNCPHFRHZCPS-UHFFFAOYSA-N di(imidazol-1-yl)methanethione Chemical compound C1=CN=CN1C(=S)N1C=CN=C1 RAFNCPHFRHZCPS-UHFFFAOYSA-N 0.000 description 6
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- 239000000273 veterinary drug Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
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Classifications
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- 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
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
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- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/13—Amines
- A61K31/131—Amines acyclic
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- 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
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- 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
- A61K31/13—Amines
-
- 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
- A61K31/13—Amines
- A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
- A61K31/137—Arylalkylamines, e.g. amphetamine, epinephrine, salbutamol, ephedrine or methadone
-
- 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
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/18—Sulfonamides
-
- 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
-
- 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
- A61K31/4245—Oxadiazoles
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/443—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with oxygen as a ring hetero atom
-
- 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
- A61K31/66—Phosphorus compounds
- A61K31/662—Phosphorus acids or esters thereof having P—C bonds, e.g. foscarnet, trichlorfon
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/16—Otologicals
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Emergency Medicine (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US35363202P | 2002-01-31 | 2002-01-31 | |
| US60/353,632 | 2002-01-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN1625393A true CN1625393A (zh) | 2005-06-08 |
Family
ID=27663234
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNA038031388A Pending CN1625393A (zh) | 2002-01-31 | 2003-01-20 | 治疗耳鸣的α2δ配体 |
Country Status (16)
| Country | Link |
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| US (2) | US7026505B2 (enExample) |
| EP (1) | EP1469841A1 (enExample) |
| JP (1) | JP2005521664A (enExample) |
| KR (1) | KR20040081478A (enExample) |
| CN (1) | CN1625393A (enExample) |
| AU (1) | AU2003201716B2 (enExample) |
| BR (1) | BR0307411A (enExample) |
| CA (1) | CA2474000A1 (enExample) |
| CL (1) | CL2008000613A1 (enExample) |
| IL (1) | IL162028A0 (enExample) |
| MX (1) | MXPA04004105A (enExample) |
| NZ (1) | NZ532624A (enExample) |
| PL (1) | PL371944A1 (enExample) |
| TW (1) | TW200306177A (enExample) |
| WO (1) | WO2003063845A1 (enExample) |
| ZA (1) | ZA200403069B (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101260063A (zh) * | 2008-03-21 | 2008-09-10 | 北京润德康医药技术有限公司 | γ-氨基丁酸衍生物及其制备方法 |
| CN111718379A (zh) * | 2019-03-19 | 2020-09-29 | 海南长安国际制药有限公司 | 具有l1和l2结构的铂类物质及其制备方法和应用 |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6001876A (en) | 1996-07-24 | 1999-12-14 | Warner-Lambert Company | Isobutylgaba and its derivatives for the treatment of pain |
| US8048917B2 (en) | 2005-04-06 | 2011-11-01 | Xenoport, Inc. | Prodrugs of GABA analogs, compositions and uses thereof |
| WO2004078734A1 (en) | 2003-03-07 | 2004-09-16 | Warner-Lambert Company Llc | TETRAZOLE AND OXADIAZOLONE SUBSTITUTED β-AMINO ACID DERIVATIVES |
| PL1622569T3 (pl) | 2003-04-24 | 2016-06-30 | Incyte Holdings Corp | Pochodne aza spiro alkanów jako inhibitory metaloproteaz |
| WO2005013888A2 (en) * | 2003-05-14 | 2005-02-17 | Cytokinetics, Inc. | Compounds, compositions and methods |
| US7727978B2 (en) | 2006-08-24 | 2010-06-01 | Bristol-Myers Squibb Company | Cyclic 11-beta hydroxysteroid dehydrogenase type I inhibitors |
| CN101506140B (zh) * | 2006-08-24 | 2014-06-18 | 百时美施贵宝公司 | 环状11β-羟类固醇脱氢酶Ⅰ型抑制剂 |
| MX2009005114A (es) * | 2006-11-14 | 2009-07-16 | Xenoport Inc | Uso de los profarmacos gabapentina y pregabalina para tratar el tinnitus. |
| EA200970487A1 (ru) * | 2006-12-08 | 2009-12-30 | Ксенопорт, Инк. | Применение пролекарств аналогов гамк для лечения заболеваний |
| ITMI20071492A1 (it) | 2007-07-24 | 2009-01-25 | S I I T Srl Servizio Internazi | "composizioni per il trattamento e la prevenzione di condizioni di vertigine e acufeni comprendenti citicolina, estratto di ginkgo biloba e flavoni dimerici di ginkgo biloba" |
| US8119658B2 (en) | 2007-10-01 | 2012-02-21 | Bristol-Myers Squibb Company | Triazolopyridine 11-beta hydroxysteroid dehydrogenase type I inhibitors |
| SG157299A1 (en) | 2008-05-09 | 2009-12-29 | Agency Science Tech & Res | Diagnosis and treatment of kawasaki disease |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2460891C2 (de) | 1974-12-21 | 1982-09-23 | Gödecke AG, 1000 Berlin | 1-Aminomethyl-1-cycloalkanessigsäuren und deren Ester, Verfahren zu deren Herstellung und diese Verbindungen enthaltende Arzneimittel |
| US4087544A (en) | 1974-12-21 | 1978-05-02 | Warner-Lambert Company | Treatment of cranial dysfunctions using novel cyclic amino acids |
| US6197819B1 (en) * | 1990-11-27 | 2001-03-06 | Northwestern University | Gamma amino butyric acid analogs and optical isomers |
| AU733896B2 (en) * | 1996-10-23 | 2001-05-31 | Warner-Lambert Company | Substituted gamma aminobutyric acids as pharmaceutical agents |
| EP1475371A1 (en) * | 1997-12-16 | 2004-11-10 | Warner-Lambert Company LLC | 1-substituted-1-aminomethyl-cycloalkane derivatives (= gabapentin analogues), their preparation and their use in the treatment of neurological disorders |
| CA2304967C (en) * | 1997-12-16 | 2005-06-14 | Warner-Lambert Company | 4(3)substituted-4(3)-aminomethyl-(thio)pyran or -piperidine derivatives (=gabapentin analogues), their preparation and their use in the treatment of neurological disorders |
| EP1400526A3 (en) * | 1997-12-16 | 2004-03-31 | Warner-Lambert Company LLC | ((cyclo)alkyl substituted)- gamma -aminobutyric acid derivatives (=Gaba analogues), their preparation and their use in the treatment of neurological disorders |
| KR20010043831A (ko) | 1998-05-26 | 2001-05-25 | 로즈 암스트롱, 크리스틴 에이. 트러트웨인 | 칼슘 채널의 알파2델타 서브유닛에 대한 친화력이 있는구조적으로 한정된 아미노산 화합물 |
| GB9821179D0 (en) * | 1998-09-30 | 1998-11-25 | Merck Sharp & Dohme | Therapeutic use |
| HRP20020025A2 (en) * | 1999-06-10 | 2003-12-31 | Warner Lambert Co | Mono- and disubstituted 3-propyl gamma-aminobutyric acids |
| HN2000000224A (es) * | 1999-10-20 | 2001-04-11 | Warner Lambert Co | Aminoacidos biciclicos como agentes farmaceuticos |
| US6620829B2 (en) * | 2000-10-17 | 2003-09-16 | Warner-Lambert Company | Method of treating noninflammatory cartilage damage |
-
2003
- 2003-01-20 CA CA002474000A patent/CA2474000A1/en not_active Abandoned
- 2003-01-20 AU AU2003201716A patent/AU2003201716B2/en not_active Ceased
- 2003-01-20 MX MXPA04004105A patent/MXPA04004105A/es active IP Right Grant
- 2003-01-20 IL IL16202803A patent/IL162028A0/xx unknown
- 2003-01-20 JP JP2003563539A patent/JP2005521664A/ja not_active Withdrawn
- 2003-01-20 EP EP03700417A patent/EP1469841A1/en not_active Ceased
- 2003-01-20 NZ NZ532624A patent/NZ532624A/en unknown
- 2003-01-20 KR KR10-2004-7011809A patent/KR20040081478A/ko not_active Ceased
- 2003-01-20 PL PL03371944A patent/PL371944A1/xx not_active Application Discontinuation
- 2003-01-20 BR BR0307411-0A patent/BR0307411A/pt not_active IP Right Cessation
- 2003-01-20 CN CNA038031388A patent/CN1625393A/zh active Pending
- 2003-01-20 WO PCT/IB2003/000232 patent/WO2003063845A1/en not_active Ceased
- 2003-01-29 US US10/353,367 patent/US7026505B2/en not_active Expired - Fee Related
- 2003-01-30 TW TW092102235A patent/TW200306177A/zh unknown
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2004
- 2004-04-22 ZA ZA200403069A patent/ZA200403069B/en unknown
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2005
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2008
- 2008-02-28 CL CL2008000613A patent/CL2008000613A1/es unknown
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101260063A (zh) * | 2008-03-21 | 2008-09-10 | 北京润德康医药技术有限公司 | γ-氨基丁酸衍生物及其制备方法 |
| CN101260063B (zh) * | 2008-03-21 | 2013-06-19 | 北京润德康医药技术有限公司 | γ-氨基丁酸衍生物及其制备方法 |
| CN111718379A (zh) * | 2019-03-19 | 2020-09-29 | 海南长安国际制药有限公司 | 具有l1和l2结构的铂类物质及其制备方法和应用 |
Also Published As
| Publication number | Publication date |
|---|---|
| MXPA04004105A (es) | 2004-11-29 |
| EP1469841A1 (en) | 2004-10-27 |
| PL371944A1 (en) | 2005-07-11 |
| BR0307411A (pt) | 2004-12-07 |
| KR20040081478A (ko) | 2004-09-21 |
| US20060100281A1 (en) | 2006-05-11 |
| CL2008000613A1 (es) | 2008-11-07 |
| NZ532624A (en) | 2007-05-31 |
| US20030176504A1 (en) | 2003-09-18 |
| IL162028A0 (en) | 2005-11-20 |
| WO2003063845A1 (en) | 2003-08-07 |
| JP2005521664A (ja) | 2005-07-21 |
| AU2003201716B2 (en) | 2008-04-17 |
| TW200306177A (en) | 2003-11-16 |
| ZA200403069B (en) | 2005-04-22 |
| US7138542B2 (en) | 2006-11-21 |
| CA2474000A1 (en) | 2003-08-07 |
| US7026505B2 (en) | 2006-04-11 |
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