TW200800217A - Novel compounds - Google Patents
Novel compounds Download PDFInfo
- Publication number
- TW200800217A TW200800217A TW095128952A TW95128952A TW200800217A TW 200800217 A TW200800217 A TW 200800217A TW 095128952 A TW095128952 A TW 095128952A TW 95128952 A TW95128952 A TW 95128952A TW 200800217 A TW200800217 A TW 200800217A
- Authority
- TW
- Taiwan
- Prior art keywords
- chloro
- butyl
- dione
- dihydro
- propyl
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 193
- 238000000034 method Methods 0.000 claims abstract description 106
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 24
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- 108020003175 receptors Proteins 0.000 claims abstract description 17
- 230000004913 activation Effects 0.000 claims abstract description 14
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- LRFVTYWOQMYALW-UHFFFAOYSA-N 9H-xanthine Chemical class O=C1NC(=O)NC2=C1NC=N2 LRFVTYWOQMYALW-UHFFFAOYSA-N 0.000 claims abstract description 11
- 239000000203 mixture Substances 0.000 claims description 261
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 153
- -1 C2-6 Chemical group 0.000 claims description 135
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 124
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 67
- 229910052757 nitrogen Inorganic materials 0.000 claims description 64
- 238000002360 preparation method Methods 0.000 claims description 37
- 210000004369 blood Anatomy 0.000 claims description 36
- 239000008280 blood Substances 0.000 claims description 36
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims description 24
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- 238000009472 formulation Methods 0.000 claims description 21
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- 150000005829 chemical entities Chemical class 0.000 claims description 17
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- 125000003118 aryl group Chemical group 0.000 claims description 15
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- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 6
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- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
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- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
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- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 3
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- 150000003536 tetrazoles Chemical class 0.000 claims description 3
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 3
- HSINOMROUCMIEA-FGVHQWLLSA-N (2s,4r)-4-[(3r,5s,6r,7r,8s,9s,10s,13r,14s,17r)-6-ethyl-3,7-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]-2-methylpentanoic acid Chemical compound C([C@@]12C)C[C@@H](O)C[C@H]1[C@@H](CC)[C@@H](O)[C@@H]1[C@@H]2CC[C@]2(C)[C@@H]([C@H](C)C[C@H](C)C(O)=O)CC[C@H]21 HSINOMROUCMIEA-FGVHQWLLSA-N 0.000 claims description 2
- 200000000007 Arterial disease Diseases 0.000 claims description 2
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- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 230000007812 deficiency Effects 0.000 claims description 2
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- 238000005658 halogenation reaction Methods 0.000 claims description 2
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical group C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims description 2
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- LIKBJVNGSGBSGK-UHFFFAOYSA-N iron(3+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Fe+3].[Fe+3] LIKBJVNGSGBSGK-UHFFFAOYSA-N 0.000 claims 1
- 230000008569 process Effects 0.000 abstract description 19
- 101000843809 Homo sapiens Hydroxycarboxylic acid receptor 2 Proteins 0.000 abstract description 15
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- 229940083747 low-ceiling diuretics xanthine derivative Drugs 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 492
- 235000019439 ethyl acetate Nutrition 0.000 description 242
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 186
- 239000000243 solution Substances 0.000 description 125
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 117
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 106
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 103
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 97
- 239000000047 product Substances 0.000 description 78
- 239000007787 solid Substances 0.000 description 78
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 62
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 52
- 239000002585 base Substances 0.000 description 51
- 206010057190 Respiratory tract infections Diseases 0.000 description 50
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 50
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 46
- 239000012044 organic layer Substances 0.000 description 46
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 37
- NFHFRUOZVGFOOS-UHFFFAOYSA-N Pd(PPh3)4 Substances [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 35
- 238000002414 normal-phase solid-phase extraction Methods 0.000 description 35
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- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 34
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 33
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- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 26
- UXRDAJMOOGEIAQ-CKOZHMEPSA-N [(8r,9s,10r,13s,14s,17r)-17-acetyl-10,13-dimethyl-16-methylidene-3-oxo-1,2,8,9,11,12,14,15-octahydrocyclopenta[a]phenanthren-17-yl] acetate Chemical compound C1=CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC(=C)[C@](OC(=O)C)(C(C)=O)[C@@]1(C)CC2 UXRDAJMOOGEIAQ-CKOZHMEPSA-N 0.000 description 26
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 26
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- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 21
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 20
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
- C07D473/04—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms
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- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
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- A61P13/12—Drugs for disorders of the urinary system of the kidneys
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- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
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- A—HUMAN NECESSITIES
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- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
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- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/48—Drugs for disorders of the endocrine system of the pancreatic hormones
- A61P5/50—Drugs for disorders of the endocrine system of the pancreatic hormones for increasing or potentiating the activity of insulin
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- A—HUMAN NECESSITIES
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- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
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- A61P9/00—Drugs for disorders of the cardiovascular system
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- A61P9/00—Drugs for disorders of the cardiovascular system
- 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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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/08—Vasodilators for multiple indications
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- A—HUMAN NECESSITIES
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- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
- C07D473/04—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms
- C07D473/06—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms with radicals containing only hydrogen and carbon atoms, attached in position 1 or 3
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- Chemical & Material Sciences (AREA)
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- Veterinary Medicine (AREA)
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- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
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- Chemical Kinetics & Catalysis (AREA)
- Diabetes (AREA)
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- Vascular Medicine (AREA)
- Rheumatology (AREA)
- Emergency Medicine (AREA)
- Nutrition Science (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
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| GB0607736A GB0607736D0 (en) | 2006-04-19 | 2006-04-19 | Novel compounds |
| GB0614569A GB0614569D0 (en) | 2006-07-21 | 2006-07-21 | Novel compounds |
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| TW095128952A TW200800217A (en) | 2005-08-10 | 2006-08-08 | Novel compounds |
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Families Citing this family (43)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7495005B2 (en) * | 2002-08-22 | 2009-02-24 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Xanthine derivatives, their preparation and their use in pharmaceutical compositions |
| CA2556073C (en) * | 2004-02-14 | 2012-01-10 | Smithkline Beecham Corporation | 8-chloro-1,3-disubstituted xanthine derivatives as hm74a receptor modulators |
| DE102004030502A1 (de) | 2004-06-24 | 2006-01-12 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue Imidazole und Triazole, deren Herstellung und Verwendung als Arzneimittel |
| JP2009504592A (ja) * | 2005-08-10 | 2009-02-05 | スミスクライン・ビーチャム・コーポレイション | 選択的ｈｍ７４ａアゴニストとしてのキサンチン誘導体 |
| JP5274455B2 (ja) | 2006-06-23 | 2013-08-28 | インサイト コーポレイション | Ｈｍ７４ａアゴニストとしてのプリノン誘導体 |
| AU2007260851B2 (en) | 2006-06-23 | 2013-01-17 | Incyte Corporation | Purinone derivatives as HM74a agonists |
| AU2007283113A1 (en) | 2006-08-08 | 2008-02-14 | Sanofi-Aventis | Arylaminoaryl-alkyl-substituted imidazolidine-2,4-diones, processes for preparing them, medicaments comprising these compounds, and their use |
| EP2025674A1 (de) | 2007-08-15 | 2009-02-18 | sanofi-aventis | Substituierte Tetrahydronaphthaline, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
| DE102007054497B3 (de) | 2007-11-13 | 2009-07-23 | Sanofi-Aventis Deutschland Gmbh | Neue kristalline Diphenylazetidinonhydrate und Verfahren zu deren Herstellung |
| UY31968A (es) | 2008-07-09 | 2010-01-29 | Sanofi Aventis | Nuevos derivados heterocíclicos, sus procesos para su preparación, y sus usos terapéuticos |
| WO2010068601A1 (en) | 2008-12-08 | 2010-06-17 | Sanofi-Aventis | A crystalline heteroaromatic fluoroglycoside hydrate, processes for making, methods of use and pharmaceutical compositions thereof |
| JP5666464B2 (ja) | 2008-12-08 | 2015-02-12 | グラクソスミスクライン・リミテッド・ライアビリティ・カンパニーＧｌａｘｏＳｍｉｔｈＫｌｉｎｅ ＬＬＣ | 新規化合物 |
| KR20120060207A (ko) | 2009-08-26 | 2012-06-11 | 사노피 | 신규한 결정성 헤테로방향족 플루오로글리코시드 수화물, 이들 화합물을 포함하는 약제 및 이들의 용도 |
| WO2011107494A1 (de) | 2010-03-03 | 2011-09-09 | Sanofi | Neue aromatische glykosidderivate, diese verbindungen enthaltende arzneimittel und deren verwendung |
| KR101799429B1 (ko) * | 2010-05-03 | 2017-11-21 | 에스케이바이오팜 주식회사 | 신경 세포 사멸 또는 신경 퇴화를 억제하기 위한 약학적 조성물 |
| EP2582709B1 (de) | 2010-06-18 | 2018-01-24 | Sanofi | Azolopyridin-3-on-derivate als inhibitoren von lipasen und phospholipasen |
| US8530413B2 (en) | 2010-06-21 | 2013-09-10 | Sanofi | Heterocyclically substituted methoxyphenyl derivatives with an oxo group, processes for preparation thereof and use thereof as medicaments |
| TW201215388A (en) | 2010-07-05 | 2012-04-16 | Sanofi Sa | (2-aryloxyacetylamino)phenylpropionic acid derivatives, processes for preparation thereof and use thereof as medicaments |
| TW201215387A (en) | 2010-07-05 | 2012-04-16 | Sanofi Aventis | Spirocyclically substituted 1,3-propane dioxide derivatives, processes for preparation thereof and use thereof as a medicament |
| TW201221505A (en) | 2010-07-05 | 2012-06-01 | Sanofi Sa | Aryloxyalkylene-substituted hydroxyphenylhexynoic acids, process for preparation thereof and use thereof as a medicament |
| PH12013500301A1 (en) * | 2010-08-16 | 2013-03-25 | Boehringer Ingelheim Int | Oxadiazole inhibitors of leukotriene production |
| WO2012040137A1 (en) * | 2010-09-23 | 2012-03-29 | Boehringer Ingelheim International Gmbh | Oxadiazole inhibitors of leukotriene production |
| EP2683704B1 (de) | 2011-03-08 | 2014-12-17 | Sanofi | Verzweigte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| US8828994B2 (en) | 2011-03-08 | 2014-09-09 | Sanofi | Di- and tri-substituted oxathiazine derivatives, method for the production thereof, use thereof as medicine and drug containing said derivatives and use thereof |
| EP2766349B1 (de) | 2011-03-08 | 2016-06-01 | Sanofi | Mit carbozyklen oder heterozyklen substituierte oxathiazinderivate, verfahren zu deren herstellung, diese verbindungen enthaltende arzneimittel und deren verwendung |
| US8871758B2 (en) | 2011-03-08 | 2014-10-28 | Sanofi | Tetrasubstituted oxathiazine derivatives, method for producing them, their use as medicine and drug containing said derivatives and the use thereof |
| US8710050B2 (en) | 2011-03-08 | 2014-04-29 | Sanofi | Di and tri- substituted oxathiazine derivatives, method for the production, method for the production thereof, use thereof as medicine and drug containing said derivatives and use thereof |
| WO2013037390A1 (en) | 2011-09-12 | 2013-03-21 | Sanofi | 6-(4-hydroxy-phenyl)-3-styryl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
| WO2013045413A1 (en) | 2011-09-27 | 2013-04-04 | Sanofi | 6-(4-hydroxy-phenyl)-3-alkyl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
| EA201492069A1 (ru) * | 2012-05-30 | 2015-03-31 | Ф.Хоффманн-Ля Рош Аг | Соединения триазола в качестве ингибиторов фосфодиэстеразы 10 (pde10) |
| PT2970303T (pt) * | 2013-03-15 | 2017-06-23 | Hydra Biosciences Inc | Xantinas substituídas e métodos de sua utilização |
| EA030958B1 (ru) | 2013-05-10 | 2018-10-31 | Джилид Аполло, Ллс | Ингибиторы акк и их применение |
| MX2015015422A (es) | 2013-05-10 | 2016-06-21 | Nimbus Apollo Inc | Inhibidores de acetil-coa carboxilasa (acc) y usos de los mismos. |
| HK1221662A1 (zh) | 2013-05-10 | 2017-06-09 | Gilead Apollo, Llc | Acc抑制剂和其用途 |
| CN105358152A (zh) | 2013-05-10 | 2016-02-24 | 尼普斯阿波罗有限公司 | Acc抑制剂和其用途 |
| CN105646492B (zh) * | 2014-11-14 | 2019-04-09 | 中国医学科学院药物研究所 | 含五元芳杂环的取代黄嘌呤类化合物及其制备方法和用途 |
| DE102017000359A1 (de) | 2016-08-26 | 2018-03-01 | Bihl+Wiedemann Gmbh | Diagnose-Repeater für AS-Interface Netze |
| WO2018162607A1 (en) * | 2017-03-07 | 2018-09-13 | F. Hoffmann-La Roche Ag | Oxadiazole transient receptor potential channel inhibitors |
| WO2020033919A1 (en) | 2018-08-10 | 2020-02-13 | Diapin Therapeutics, Llc | Tri-peptides and treatment of metabolic, cardiovascular and inflammatory disorders |
| CN112724141A (zh) * | 2021-01-21 | 2021-04-30 | 南京艾美斐生物医药科技有限公司 | 一种gpr109a蛋白受体抑制剂及其制备和应用 |
| MX2024009581A (es) * | 2022-02-03 | 2024-08-13 | De Shaw Res Llc | Compuestos de uracilo n3-sustituidos como inhibidores de trpa1. |
| AR131717A1 (es) * | 2023-01-30 | 2025-04-23 | De Shaw Res Llc | Compuestos de imida biciclica como inhibidores de trpa1 |
| AR133217A1 (es) * | 2023-07-10 | 2025-09-10 | De Shaw Res Llc | Inhibidores de trpa1 bicíclicos y monocíclicos |
Family Cites Families (40)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2797220A (en) * | 1954-12-02 | 1957-06-25 | Univ Michigan | Substituted paraxanthines |
| GB8906792D0 (en) * | 1989-03-23 | 1989-05-10 | Beecham Wuelfing Gmbh & Co Kg | Treatment and compounds |
| NZ240644A (en) | 1990-11-21 | 1994-08-26 | Smithkline Beecham Corp | Use of xanthine derivatives to inhibit the production of tumour necrosis factor (tnf) |
| AU3725893A (en) | 1992-02-21 | 1993-09-13 | Smithkline Beecham Corporation | TNF inhibitors |
| DK0584347T3 (da) | 1992-03-04 | 2003-02-24 | Cell Therapeutics Inc | Enantiomere hydroxylerede xanthinforbindelser |
| US5473070A (en) | 1992-11-16 | 1995-12-05 | Cell Therapeutics, Inc. | Substituted long chain alcohol xanthine compounds |
| US5780476A (en) * | 1992-11-16 | 1998-07-14 | Cell Therapeutics, Inc. | Hydroxyl-containing xanthine compounds |
| US6693105B1 (en) * | 1992-11-16 | 2004-02-17 | Cell Therapeutics, Inc. | Hydroxyl-containing compounds |
| US6469017B1 (en) | 1998-01-16 | 2002-10-22 | Cell Therapeutics, Inc. | Method of inhibiting interleukin-12 signaling |
| IL109161A0 (en) | 1993-03-31 | 1994-06-24 | Cell Therapeutics Inc | Amino alcohol derivatives, methods for the preparation thereof, and pharmaceutical compositions containing the same |
| US5670506A (en) | 1993-04-05 | 1997-09-23 | Cell Therapeutics, Inc. | Halogen, isothiocyanate or azide substituted xanthines |
| AU6702894A (en) | 1993-04-09 | 1994-11-08 | Cell Therapeutics, Inc. | Ring-substituted cell signaling inhibitors |
| WO1995020589A1 (en) | 1994-01-28 | 1995-08-03 | Cell Therapeutics, Inc. | Cell signaling inhibitors |
| US6878715B1 (en) * | 1994-02-18 | 2005-04-12 | Cell Therapeutics, Inc. | Therapeutic compounds for inhibiting interleukin-12 signals and method for using same |
| EP0746557A4 (en) * | 1994-02-18 | 1997-05-02 | Cell Therapeutics Inc | INTRACELLULAR SIGNALING MEDIATORS |
| US6103730A (en) * | 1994-03-24 | 2000-08-15 | Cell Therapeutics, Inc. | Amine substituted compounds |
| US6780865B1 (en) * | 1994-02-18 | 2004-08-24 | Cell Therapeutics, Inc. | Compounds having selective hydrolytic potentials |
| US5807861A (en) * | 1994-03-24 | 1998-09-15 | Cell Therapeutics, Inc. | Amine substituted xanthinyl compounds |
| US6323201B1 (en) * | 1994-12-29 | 2001-11-27 | The Regents Of The University Of California | Compounds for inhibition of ceramide-mediated signal transduction |
| AR015966A1 (es) | 1997-10-17 | 2001-05-30 | Smithkline Beecham Corp | Uso de un compuesto inhibidor de pde4 para la preparacion de un medicamento util para el tratamiento de prurito |
| MXPA01010143A (es) | 1999-04-09 | 2003-07-14 | Cell Therapeutics Inc | Derivados de xantina y analogos como inhibidores de transmision de senales celulares. |
| US20030207901A1 (en) * | 1999-07-27 | 2003-11-06 | Cell Therapeutics, Inc. | Hydroxyl-containing compounds |
| US6821978B2 (en) * | 2000-09-19 | 2004-11-23 | Schering Corporation | Xanthine phosphodiesterase V inhibitors |
| US6586429B2 (en) * | 2000-11-29 | 2003-07-01 | Cell Therapeutics, Inc. | Tricyclic fused xanthine compounds and their uses |
| EA007485B1 (ru) * | 2001-02-24 | 2006-10-27 | Берингер Ингельхайм Фарма Гмбх Унд Ко. Кг | Производные ксантина, способ их получения, фармацевтическая композиция на их основе и способ ее получения |
| US20040254224A1 (en) | 2001-04-11 | 2004-12-16 | Foord Steven Michael | Medicaments |
| EP1404675B1 (en) * | 2001-07-03 | 2008-03-12 | Novo Nordisk A/S | Dpp-iv-inhibiting purine derivatives for the treatment of diabetes |
| EP1338595B1 (en) * | 2002-02-25 | 2006-05-03 | Eisai Co., Ltd. | Xanthine derivatives as DPP-IV inhibitors |
| US7482337B2 (en) * | 2002-11-08 | 2009-01-27 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Xanthine derivatives, the preparation thereof and their use as pharmaceutical compositions |
| CN1227492C (zh) * | 2003-03-11 | 2005-11-16 | 张跃 | 一种吸收式空调主体 |
| GB0319124D0 (en) * | 2003-08-14 | 2003-09-17 | Smithkline Beecham Corp | Chemical compounds |
| CA2556073C (en) * | 2004-02-14 | 2012-01-10 | Smithkline Beecham Corporation | 8-chloro-1,3-disubstituted xanthine derivatives as hm74a receptor modulators |
| WO2006045564A1 (en) * | 2004-10-22 | 2006-05-04 | Smithkline Beecham Corporation | Xanthine derivatives with hm74a receptor activity |
| US20090209561A1 (en) * | 2004-10-22 | 2009-08-20 | Richard Jonathan Daniel Hatley | Xanthine Derivatives with HM74A Receptor Activity |
| MX2007004882A (es) * | 2004-10-22 | 2007-05-09 | Smithkline Beecham Corp | Derivados de xantina con actividad de receptor de hm74a. |
| JP2008530074A (ja) * | 2005-02-14 | 2008-08-07 | スミスクライン・ビーチャム・コーポレイション | Ｈｍ７４ａ受容体アゴニストとしてのアントラニル酸誘導体 |
| GB0516462D0 (en) * | 2005-08-10 | 2005-09-14 | Smithkline Beecham Corp | Novel compounds |
| JP2009504592A (ja) * | 2005-08-10 | 2009-02-05 | スミスクライン・ビーチャム・コーポレイション | 選択的ｈｍ７４ａアゴニストとしてのキサンチン誘導体 |
| DE102008009758A1 (de) * | 2008-02-18 | 2009-08-20 | Beiersdorf Ag | Verwendung von 3-(4-Hydroxy-3-methoxyphenyl)-1-(4-hydroxyphenyl)-propan-1-on zur verbesserten Hautkonturierung bzw. gegen Cellulite |
| JP5666464B2 (ja) | 2008-12-08 | 2015-02-12 | グラクソスミスクライン・リミテッド・ライアビリティ・カンパニーＧｌａｘｏＳｍｉｔｈＫｌｉｎｅ ＬＬＣ | 新規化合物 |
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2006
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- 2006-08-08 EP EP06763016A patent/EP1912991B1/en not_active Not-in-force
- 2006-08-08 PT PT06763016T patent/PT1912991E/pt unknown
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- 2006-08-08 AU AU2006278216A patent/AU2006278216A1/en not_active Abandoned
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- 2006-08-08 AR ARP060103459A patent/AR055369A1/es unknown
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2008
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- 2008-02-21 CR CR9749A patent/CR9749A/es not_active Application Discontinuation
- 2008-03-07 NO NO20081211A patent/NO20081211L/no not_active Application Discontinuation
- 2008-03-07 NO NO20081212A patent/NO20081212L/no not_active Application Discontinuation
-
2011
- 2011-01-12 CY CY20111100033T patent/CY1111757T1/el unknown
- 2011-04-18 US US13/088,962 patent/US20110257205A1/en not_active Abandoned
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