UA74826C2 - ?-carboline derivatives as phosphodiesterase inhibitors - Google Patents
?-carboline derivatives as phosphodiesterase inhibitors Download PDFInfo
- Publication number
- UA74826C2 UA74826C2 UA2002119179A UA2002119179A UA74826C2 UA 74826 C2 UA74826 C2 UA 74826C2 UA 2002119179 A UA2002119179 A UA 2002119179A UA 2002119179 A UA2002119179 A UA 2002119179A UA 74826 C2 UA74826 C2 UA 74826C2
- Authority
- UA
- Ukraine
- Prior art keywords
- group
- phenyl
- nitro
- furyl
- substituted
- Prior art date
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- 239000002571 phosphodiesterase inhibitor Substances 0.000 title abstract description 5
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- 238000011282 treatment Methods 0.000 claims abstract description 40
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- 238000000034 method Methods 0.000 claims description 47
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- 229910052736 halogen Inorganic materials 0.000 claims description 26
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- 125000000217 alkyl group Chemical group 0.000 claims description 17
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- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- 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
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- A61P11/06—Antiasthmatics
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P15/10—Drugs for genital or sexual disorders; Contraceptives for impotence
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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
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/24—Drugs for disorders of the endocrine system of the sex hormones
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
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- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Endocrinology (AREA)
- Pulmonology (AREA)
- Reproductive Health (AREA)
- Diabetes (AREA)
- Hospice & Palliative Care (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Hematology (AREA)
- Gynecology & Obstetrics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US20466700P | 2000-05-17 | 2000-05-17 | |
| PCT/US2001/014357 WO2001087038A2 (en) | 2000-05-17 | 2001-05-03 | β-CARBOLINE DERIVATIVES USEFUL AS INHIBITORS OF PHOSPHODIESTERASE |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| UA74826C2 true UA74826C2 (en) | 2006-02-15 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| UA2002119179A UA74826C2 (en) | 2000-05-17 | 2001-03-05 | ?-carboline derivatives as phosphodiesterase inhibitors |
Country Status (32)
| Country | Link |
|---|---|
| US (2) | US6492358B2 (es) |
| EP (1) | EP1289985B1 (es) |
| JP (1) | JP5014551B2 (es) |
| KR (1) | KR20030031482A (es) |
| CN (1) | CN1255403C (es) |
| AR (1) | AR028576A1 (es) |
| AT (1) | ATE256127T1 (es) |
| AU (2) | AU6116701A (es) |
| BG (1) | BG66141B1 (es) |
| CA (1) | CA2409715C (es) |
| CZ (1) | CZ20023934A3 (es) |
| DE (1) | DE60101479T2 (es) |
| DK (1) | DK1289985T3 (es) |
| ES (1) | ES2211806T3 (es) |
| GE (1) | GEP20053511B (es) |
| HK (1) | HK1051368A1 (es) |
| HR (1) | HRP20020910B1 (es) |
| HU (1) | HUP0302412A3 (es) |
| IL (2) | IL152873A0 (es) |
| MX (1) | MXPA02011426A (es) |
| MY (1) | MY128479A (es) |
| NO (1) | NO324251B1 (es) |
| NZ (1) | NZ522731A (es) |
| PL (1) | PL205507B1 (es) |
| PT (1) | PT1289985E (es) |
| RU (1) | RU2271358C2 (es) |
| SK (1) | SK16972002A3 (es) |
| TR (1) | TR200302309T4 (es) |
| TW (1) | TWI286553B (es) |
| UA (1) | UA74826C2 (es) |
| WO (1) | WO2001087038A2 (es) |
| ZA (1) | ZA200210111B (es) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2002062339A1 (en) * | 2000-12-08 | 2002-08-15 | Smithkline Beecham Corporation | Antibacterial compounds |
| US6900220B2 (en) * | 2001-01-02 | 2005-05-31 | Syntex (U.S.A.) Llc | Quinazolone derivatives as alpha 1A/B adrenergic receptor antagonists |
| WO2002064590A2 (en) * | 2001-02-12 | 2002-08-22 | Lilly Icos Llc | Carboline derivatives |
| JP4223285B2 (ja) * | 2001-02-12 | 2009-02-12 | リリー アイコス リミテッド ライアビリティ カンパニー | 化合物 |
| US7115621B2 (en) * | 2001-04-25 | 2006-10-03 | Lilly Icos Llc | Chemical compounds |
| JP2004536816A (ja) | 2001-06-05 | 2004-12-09 | リリー アイコス リミテッド ライアビリティ カンパニー | Ｐｄｅ５阻害剤としてのカルボリン誘導体 |
| MXPA03011167A (es) * | 2001-06-21 | 2004-02-26 | Lilly Icos Llc | Derivados de carbolina utiles como ihibidores de pdev. |
| CN1280292C (zh) | 2001-11-14 | 2006-10-18 | 奥索-麦克尼尔药品公司 | 用作磷酸二酯酶抑制剂的被取代的四环吡咯并喹诺酮衍生物 |
| BRPI0307699A2 (pt) * | 2002-02-07 | 2015-06-16 | Gtx Inc | Tratamento de hiperplasia benigna da próstata com sarms. |
| ES2297217T3 (es) * | 2002-06-19 | 2008-05-01 | Janssen Pharmaceutica Nv | Derivados sustituidos de 2,4-dihidro-pirrolo(3,4-b)quinolin-9-ona utilizados como inhibidores de fosfodiesterasa. |
| US7872133B2 (en) * | 2003-06-23 | 2011-01-18 | Ono Pharmaceutical Co., Ltd. | Tricyclic heterocycle compound |
| AU2005206570A1 (en) | 2004-01-23 | 2005-08-04 | Novartis Vaccines And Diagnostics, Inc. | Tetrahydrocarboline compounds as anticancer agents |
| SG184755A1 (en) | 2004-03-15 | 2012-10-30 | Ptc Therapeutics Inc | Carboline derivatives useful in the inhibition of angiogenesis |
| US7767689B2 (en) | 2004-03-15 | 2010-08-03 | Ptc Therapeutics, Inc. | Carboline derivatives useful in the treatment of cancer |
| US8076352B2 (en) | 2004-03-15 | 2011-12-13 | Ptc Therapeutics, Inc. | Administration of carboline derivatives useful in the treatment of cancer and other diseases |
| US8076353B2 (en) | 2004-03-15 | 2011-12-13 | Ptc Therapeutics, Inc. | Inhibition of VEGF translation |
| AR051780A1 (es) * | 2004-11-29 | 2007-02-07 | Japan Tobacco Inc | Compuestos en anillo fusionados que contienen nitrogeno y utilizacion de los mismos |
| WO2006068164A1 (ja) * | 2004-12-22 | 2006-06-29 | Ono Pharmaceutical Co., Ltd. | 三環式化合物およびその用途 |
| GB2422828A (en) * | 2005-02-03 | 2006-08-09 | Hunter Fleming Ltd | Tricyclic cytoprotective compounds comprising an indole residue |
| KR20080047375A (ko) * | 2005-07-29 | 2008-05-28 | 콘서트 파마슈티컬즈, 인크. | 약제 화합물 |
| EP2258359A3 (en) | 2005-08-26 | 2011-04-06 | Braincells, Inc. | Neurogenesis by muscarinic receptor modulation with sabcomelin |
| JP2009506069A (ja) | 2005-08-26 | 2009-02-12 | ブレインセルス，インコーポレイティド | ムスカリン性受容体調節による神経発生 |
| AU2006304787A1 (en) | 2005-10-21 | 2007-04-26 | Braincells, Inc. | Modulation of neurogenesis by PDE inhibition |
| CA2625210A1 (en) | 2005-10-31 | 2007-05-10 | Braincells, Inc. | Gaba receptor mediated modulation of neurogenesis |
| US20100216734A1 (en) | 2006-03-08 | 2010-08-26 | Braincells, Inc. | Modulation of neurogenesis by nootropic agents |
| AU2007249399A1 (en) | 2006-05-09 | 2007-11-22 | Braincells, Inc. | Neurogenesis by modulating angiotensin |
| US7678808B2 (en) | 2006-05-09 | 2010-03-16 | Braincells, Inc. | 5 HT receptor mediated neurogenesis |
| EP2068872A1 (en) * | 2006-09-08 | 2009-06-17 | Braincells, Inc. | Combinations containing a 4-acylaminopyridine derivative |
| US20100184806A1 (en) | 2006-09-19 | 2010-07-22 | Braincells, Inc. | Modulation of neurogenesis by ppar agents |
| US20100184758A1 (en) * | 2007-07-19 | 2010-07-22 | Dobbelaar Peter H | Beta carboline derivatives as antidiabetic compounds |
| EP2225250A2 (en) | 2007-11-30 | 2010-09-08 | Biota Scientific Management Pty Ltd | Bicyclic ppat inhibitors as antibacterial agents |
| ES2523580T3 (es) | 2008-01-11 | 2014-11-27 | Albany Molecular Research, Inc. | Piridoindoles substituidos con (1-Azinona) |
| CN104387382A (zh) | 2008-03-24 | 2015-03-04 | 梅迪维新技术公司 | 吡啶并[3,4-b]吲哚和应用方法 |
| MD4009C2 (ro) * | 2008-07-15 | 2010-08-31 | Институт Химии Академии Наук Молдовы | Utilizarea 1-metil-4-(N-metilaminobutil-4)-β-carbolinei în calitate de remediu antituberculos |
| WO2010099217A1 (en) | 2009-02-25 | 2010-09-02 | Braincells, Inc. | Modulation of neurogenesis using d-cycloserine combinations |
| US20120135089A1 (en) * | 2009-03-17 | 2012-05-31 | Stockwell Brent R | E3 ligase inhibitors |
| WO2011003007A1 (en) | 2009-07-01 | 2011-01-06 | Albany Molecular Research, Inc. | Azabicycloalkane-indole and azabicycloalkane-pyrrolo-pyridine mch-1 antagonists, methods of making, and use thereof |
| JP2012532144A (ja) | 2009-07-01 | 2012-12-13 | アルバニー モレキュラー リサーチ， インコーポレイテッド | アジノン置換アゼピノ［ｂ］インドールおよびピリド−ピロロ−アゼピンｍｃｈ−１拮抗薬、ならびにその作製方法および使用 |
| WO2011003012A1 (en) | 2009-07-01 | 2011-01-06 | Albany Molecular Research, Inc. | Azinone-substituted azapolycycle mch-1 antagonists, methods of making, and use thereof |
| WO2011003021A1 (en) | 2009-07-01 | 2011-01-06 | Albany Molecular Research, Inc. | Azinone-substituted azabicycloalkane-indole and azabicycloalkane-pyrrolo-pyridine mch-1 antagonists, methods of making, and use thereof |
| JP5791611B2 (ja) * | 2009-09-23 | 2015-10-07 | メディベイション テクノロジーズ， インコーポレイテッド | ピリド［３，４−ｂ］インドールおよび使用方法 |
| SG186826A1 (en) * | 2010-07-06 | 2013-02-28 | Ono Pharmaceutical Co | Tetrahydrocarboline derivative |
| US8993765B2 (en) | 2010-12-21 | 2015-03-31 | Albany Molecular Research, Inc. | Tetrahydro-azacarboline MCH-1 antagonists, methods of making, and uses thereof |
| US8697700B2 (en) | 2010-12-21 | 2014-04-15 | Albany Molecular Research, Inc. | Piperazinone-substituted tetrahydro-carboline MCH-1 antagonists, methods of making, and uses thereof |
| WO2012127885A1 (ja) | 2011-03-18 | 2012-09-27 | 小野薬品工業株式会社 | テトラヒドロカルボリン誘導体 |
| WO2013106547A1 (en) | 2012-01-10 | 2013-07-18 | President And Fellows Of Harvard College | Beta-cell replication promoting compounds and methods of their use |
| US10092574B2 (en) | 2012-09-26 | 2018-10-09 | Valorisation-Recherche, Limited Partnership | Inhibitors of polynucleotide repeat-associated RNA foci and uses thereof |
| WO2017168174A1 (en) | 2016-04-02 | 2017-10-05 | N4 Pharma Uk Limited | New pharmaceutical forms of sildenafil |
| CN107216327A (zh) * | 2017-06-27 | 2017-09-29 | 山东大学 | 5型磷酸二酯酶抑制剂及其制备方法和用途 |
| WO2021046194A1 (en) * | 2019-09-03 | 2021-03-11 | The Regents Of The University Of Colorado A Body Corporate | Tryptoline-based benzothiazoles and their use as antibiotics and antibiotic resistance-modifying agents |
| US20220296593A1 (en) * | 2020-12-11 | 2022-09-22 | Institut De Cardiologie De Montreal | Methods of treating elevated plasma cholesterol |
| EP4267578A1 (en) | 2020-12-23 | 2023-11-01 | Recurium IP Holdings, LLC | Estrogen receptor modulators |
Family Cites Families (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1055203A (en) | 1964-09-16 | 1967-01-18 | Ici Ltd | -ß-carboline derivatives, a process for their manufacture, and compositions containing them |
| US4228168A (en) | 1978-11-22 | 1980-10-14 | Tanabe Seiyaku Co., Ltd. | Azepino [1,2,3-lm]-β-carboline compounds and pharmaceutical composition thereof |
| NZ194747A (en) | 1979-08-29 | 1988-11-29 | Schering Ag | 9h-pyrido(3,4-b)indol-3-ylcarboxylic acid derivatives |
| DE3752373T2 (de) | 1986-10-13 | 2004-03-25 | Asahi Kasei Kogyo K.K. | Pyridin-derivate |
| CS262100B1 (cs) * | 1987-07-17 | 1989-02-10 | Protiva Miroslav | 1-substituované 2- [ (4-methyl-l-piperazinyl)acetyl ] -2,3,4,9- -tetrahydro-lH-pyrido( 3,4-b)indoly a jejich hydrochloridy |
| ATE136032T1 (de) | 1987-07-20 | 1996-04-15 | Duphar Int Res | 8,9-anellierte 1,2,3,4-tetrahydro-beta-carbolin- derivate |
| FR2619112B1 (fr) * | 1987-08-07 | 1989-11-17 | Synthelabo | Derives de (piperidinyl-4)methyl-2 benzo(b)furo(2,3-c) pyridines, leur preparation et leur application en therapeutique |
| US4971974A (en) | 1988-06-16 | 1990-11-20 | Neurex Corporation | Benzothiophenes as appetite suppressants |
| EP0386258A4 (en) | 1988-08-11 | 1992-05-13 | Asahi Kasei Kogyo Kabushiki Kaisha | Tetrahydropyridine derivatives |
| US5250534A (en) * | 1990-06-20 | 1993-10-05 | Pfizer Inc. | Pyrazolopyrimidinone antianginal agents |
| FR2663935A1 (fr) | 1990-06-27 | 1992-01-03 | Adir | Nouveaux 1,2,3,4,5,6-hexahydroazepino [4,5-b] indoles et 1,2,3,4-tetrahydrobethacarbolines, leurs procedes de preparation et les compositions pharmaceutiques qui les contiennent. |
| GB9311920D0 (en) | 1993-06-09 | 1993-07-28 | Pfizer Ltd | Therapeutic agents |
| GB9401090D0 (en) | 1994-01-21 | 1994-03-16 | Glaxo Lab Sa | Chemical compounds |
| US5403851A (en) | 1994-04-05 | 1995-04-04 | Interneuron Pharmaceuticals, Inc. | Substituted tryptamines, phenalkylamines and related compounds |
| ATE247114T1 (de) * | 1994-09-12 | 2003-08-15 | Lilly Co Eli | Serotonergische modulatoren |
| FR2724384B1 (fr) | 1994-09-14 | 1999-04-16 | Cemaf | Nouveaux derives de la 3,4-dihydro beta-carboline agonistes de la melatonine, leur procede de preparation et leur utilisation a titre de medicament |
| DE4436190A1 (de) | 1994-10-10 | 1996-04-11 | Gerhard Prof Dr Bringmann | Halogenierte ß-Carbolin-Derivate, Verfahren zu ihrer Herstellung und Verwendung dieser Substanzen zur Hemmung der Atmungskette |
| DE4436509A1 (de) | 1994-10-13 | 1996-04-18 | Hoechst Schering Agrevo Gmbh | Substituierte Spiroalkylamino- und alkoxy-Heterocyclen, Verfahren zu ihrer Herstellung und ihre Verwendung als Schädlingsbekämpfungsmittel und Fungizide |
| GB9423910D0 (en) | 1994-11-26 | 1995-01-11 | Pfizer Ltd | Therapeutic agents |
| GB9423911D0 (en) | 1994-11-26 | 1995-01-11 | Pfizer Ltd | Therapeutic agents |
| US5968910A (en) * | 1994-11-30 | 1999-10-19 | Jan M. R. Balzarini | Compositions containing two or three inhibitors of different HIV reverse transcriptases |
| GB9514464D0 (en) | 1995-07-14 | 1995-09-13 | Glaxo Lab Sa | Medicaments |
| FR2748026B1 (fr) | 1996-04-26 | 1998-06-05 | Adir | Nouveaux inhibiteurs de metalloproteases, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| YU49898A (sh) | 1996-05-10 | 2000-03-21 | Icos Corporation | Hemijska jedinjenja |
| US6018046A (en) | 1996-05-31 | 2000-01-25 | Mochida Pharmaceutical Co., Ltd. | Pyridocarbazole derivatives having cGMP-PDE inhibitory activity |
| WO1998040385A1 (en) | 1997-03-07 | 1998-09-17 | Novo Nordisk A/S | 4,5,6,7-TETRAHYDRO-THIENO[3,2-c]PYRIDINE DERIVATIVES, THEIR PREPARATION AND USE |
| US6043252A (en) | 1997-05-05 | 2000-03-28 | Icos Corporation | Carboline derivatives |
| WO2000002878A1 (en) | 1998-07-11 | 2000-01-20 | University Of Bristol | Compounds having activity at imidazoline receptors |
| FR2796644B1 (fr) * | 1999-07-23 | 2001-09-07 | Adir | Nouveaux derives de beta-carboline, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
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