HRP20020911B1 - Supstituirani derivati pirolopiridinona korisni kao inhibitori fosfodiesteraze - Google Patents
Supstituirani derivati pirolopiridinona korisni kao inhibitori fosfodiesterazeInfo
- Publication number
- HRP20020911B1 HRP20020911B1 HR20020911A HRP20020911A HRP20020911B1 HR P20020911 B1 HRP20020911 B1 HR P20020911B1 HR 20020911 A HR20020911 A HR 20020911A HR P20020911 A HRP20020911 A HR P20020911A HR P20020911 B1 HRP20020911 B1 HR P20020911B1
- Authority
- HR
- Croatia
- Prior art keywords
- c6alkyl
- independently selected
- group
- nhra
- substituents independently
- Prior art date
Links
- 229940082638 cardiac stimulant phosphodiesterase inhibitors Drugs 0.000 title 1
- 239000002571 phosphodiesterase inhibitor Substances 0.000 title 1
- ORKUYZDMEWAUEZ-UHFFFAOYSA-N pyrrolo[3,2-b]pyridin-2-one Chemical class N1=CC=CC2=NC(=O)C=C21 ORKUYZDMEWAUEZ-UHFFFAOYSA-N 0.000 title 1
- 125000001424 substituent group Chemical group 0.000 abstract 9
- -1 amino, acetyl Chemical group 0.000 abstract 7
- 229910052736 halogen Inorganic materials 0.000 abstract 6
- 150000002367 halogens Chemical group 0.000 abstract 6
- 125000001072 heteroaryl group Chemical group 0.000 abstract 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 4
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 3
- 125000003118 aryl group Chemical group 0.000 abstract 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 3
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 abstract 2
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 abstract 2
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 abstract 2
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 2
- 125000000592 heterocycloalkyl group Chemical group 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 2
- 125000004043 oxo group Chemical group O=* 0.000 abstract 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 abstract 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 1
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 abstract 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 125000005842 heteroatom Chemical group 0.000 abstract 1
- 125000001624 naphthyl group Chemical group 0.000 abstract 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
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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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/02—Drugs for genital or sexual disorders; Contraceptives for disorders of the vagina
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/06—Antiabortive agents; Labour repressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/08—Drugs for genital or sexual disorders; Contraceptives for gonadal disorders or for enhancing fertility, e.g. inducers of ovulation or of spermatogenesis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/10—Drugs for genital or sexual disorders; Contraceptives for impotence
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
-
- 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
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Cardiology (AREA)
- Diabetes (AREA)
- Heart & Thoracic Surgery (AREA)
- Gynecology & Obstetrics (AREA)
- Hematology (AREA)
- Pulmonology (AREA)
- Pregnancy & Childbirth (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Emergency Medicine (AREA)
- Obesity (AREA)
- Hospice & Palliative Care (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
Spoj formule (I) ili (II): naznačen time, daR1 sebira iz skupine koja obuhvaća vodik, karboksi, -C(O)-C1-C6-alkil, -C(O)-C1-C6alkoksi, -C(O)-NH-C1-C6alkil-NH2, -C(O)-NH-C1-C6alkil-NHRA, -C(O)-NH-C1-C6alkil-N(RA)2, -C(O)-NH2, -C(O)-NHRA, -C(O)-N(RA)2, -C1-C6alkil-NH2, -C1-C6alkil-NHRA, -C1-C6alkil-N(RA)2, -NH-C1-C6alkil-N(RA)2;pri čemu se svaki RAnezavisno bira iz skupine koja obuhvaća C1-C6-alkil, aril, C1-C6aralkil i heteroaril, pri čemu se aril, aralkil ili heteroaril mogu opcionalno supstituirati s jednim do tri RB;pri čemu se svaki RB nezavisno bira iz skupine koja obuhvaća halogen, nitro, cijano, C1-C6alkil, C1-C6alkoksi, C1-C6alkil karboni1, karboksi C1-C6alkil, C1-C6alkilsulfonil, trifluormetil, amino, di(C1-C6alkil)amino, acetilamino, karboksiC1-C6alkilkarbonilamino, hidroksiC1-C6alkilamino, NHRA i N(RA)2;R2 se bira iz skupine koja obuhvaća C5-C10alkil (koji se može supstituirati s jednim do tri supstituenta koji se nezavisnobiraju između halogena, hidroksi, nitro, amino, NHRA ili N(RA)2, aril (moguće supstituiran s jednimdo tri supstituenta koji se nezavisno biraju između Rc), cikloalkil (moguće supstituiran s jednim do tri supstituenta koji se nezavisno biraju izmeđuRA), heteroaril (moguće supstituiran s jednim do tri supstituenta nezavisno izabrana između Rc), i heterocikloalkil (moguće supstituiran s jednim do tri supstituenta koji se nezavisno biraju između Rc);pri čemu se Rc bira iz skupine koja obuhvaća halogen, nitro, cijano, C1-C6alkil, C1-C6alkoksi, trifluormetil, trifluormetoksi, NH2, NH(C1-C6alkil) i N (C1-C6alkil)2;R3 se bira iz skupine koja obuhvaća vodik, C1-C6alkil, C1-C6alkilkarboni1, C2-C6alkenilkarboni1 i C2-C6alkinilkarbonil; b je cijeli broj od 0 do 4; R4 se nezavisno bira iz skupine koja obuhvaća halogen, hidroksi, karboksi, okso, nitro, C1-C6alkil, C1-C6alkoksi, C1-C6alkoksikarbonil, trifluormetil, fenil (pri čemu se fenilna skupina može supstituirati s jednim do tri supstituenta koji se nezavisno biraju između RD), fenilsulfonil, naftil, C1-C6aralkil, -O-aralkil, (pri čemu se aralkilna skupina može supstituirati s jednim do tri supstituenta koji se nezavisno biraju između RD), heteroaril (pri čemu se heteroaril može supstituirati s jednim do tri supstituenta koji se nezavisno biraju između RD), heterocikloalkil, NH2, pri čemu se svaki RD nezavisno bira između halogena, hidroksi, karboksi, okso, C1-C4alkila, C1-C4alkiltio, hidroksi C1-C4-alkila, C1-C4alkoksi, C1-C4alkiloksikarbonila, C1-C4alkilkarbonila, trifluormetila,trifluormetoksi, NH2, NHRA, N(RA)2, C(O)N(RA)2, SO2N(RA)2, acetilamino, nitro, cijano, formila, C1-C6alkilsulfonila, karboksi C1-C6alkila i aralkila;c je cijeli broj od 0 do 4; R5 se nezavisno bira iz skupine koja obuhvaća halogen, nitro, hidroksi,C1-C6alkil, C1-C6alkoksi, -NH2, -NHRA, -N(RA)2, -ORA, -C(O)NH2, -C(O)NHRA, -C(O)N(RA)2, -NHC(O)RA, -SO2NHRA, -SO2N(RA)2, pri čemu je RA kako je gore definiran, fenil (moguće supstituiran s jednim do tri supstituenta koji se nezavisno biraju između RB), heter
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US20464600P | 2000-05-17 | 2000-05-17 | |
| PCT/US2001/014391 WO2001087882A2 (en) | 2000-05-17 | 2001-05-03 | Substituted pyrrolopyridinone derivatives useful as phosphodiesterase inhibitors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| HRP20020911A2 HRP20020911A2 (en) | 2004-12-31 |
| HRP20020911B1 true HRP20020911B1 (hr) | 2009-01-31 |
Family
ID=22758822
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR20020911A HRP20020911B1 (hr) | 2000-05-17 | 2002-11-15 | Supstituirani derivati pirolopiridinona korisni kao inhibitori fosfodiesteraze |
Country Status (29)
| Country | Link |
|---|---|
| US (3) | US6635638B2 (hr) |
| EP (1) | EP1296981B1 (hr) |
| JP (1) | JP5366349B2 (hr) |
| KR (2) | KR20030031483A (hr) |
| CN (1) | CN1280291C (hr) |
| AR (1) | AR028575A1 (hr) |
| AT (1) | ATE278690T1 (hr) |
| AU (1) | AU6117801A (hr) |
| BG (1) | BG65925B1 (hr) |
| CA (1) | CA2409743C (hr) |
| CZ (1) | CZ20023945A3 (hr) |
| DE (1) | DE60106252T2 (hr) |
| ES (1) | ES2230316T3 (hr) |
| GE (1) | GEP20053510B (hr) |
| HK (1) | HK1054034B (hr) |
| HR (1) | HRP20020911B1 (hr) |
| HU (1) | HUP0302226A3 (hr) |
| IL (2) | IL152872A0 (hr) |
| MX (1) | MXPA02011425A (hr) |
| MY (1) | MY126917A (hr) |
| NO (1) | NO324843B1 (hr) |
| NZ (1) | NZ522732A (hr) |
| PL (1) | PL363150A1 (hr) |
| PT (1) | PT1296981E (hr) |
| RU (1) | RU2267490C2 (hr) |
| SK (1) | SK286992B6 (hr) |
| UA (1) | UA72611C2 (hr) |
| WO (1) | WO2001087882A2 (hr) |
| ZA (1) | ZA200210114B (hr) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| UA72611C2 (uk) * | 2000-05-17 | 2005-03-15 | Орто-Макнейл Фармацевтикал, Інк. | Похідні заміщеного піролопіридинону, корисні як інгібітори фосфодіестерази |
| DE60112974T2 (de) | 2001-02-12 | 2006-02-16 | Lilly Icos Llc, Wilmington | Carbolinderivate |
| US7122554B2 (en) | 2001-02-12 | 2006-10-17 | Lilly Icos Llc. | Carboline derivatives |
| WO2003042213A1 (en) * | 2001-11-14 | 2003-05-22 | Ortho-Mcneil Pharmaceutical Corporation | Substituted tetracyclic pyrroloquinolone derivatives useful as phosphodiesterase inhibitors |
| US6800625B2 (en) * | 2002-06-19 | 2004-10-05 | Janssen Pharmaceutica N.V. | Substituted 2,4-dihydro-pyrrolo[3,4-b]quinolin-9-one derivatives useful as phosphodiesterase inhibitors |
| US7045652B2 (en) * | 2002-07-03 | 2006-05-16 | Pfizer Inc | Processes for preparing substituted aryl boronic acids |
| US8076353B2 (en) | 2004-03-15 | 2011-12-13 | Ptc Therapeutics, Inc. | Inhibition of VEGF translation |
| KR101188778B1 (ko) | 2004-03-15 | 2012-10-10 | 피티씨 테라퓨틱스, 인크. | 혈관형성을 억제하는데 유용한 카르볼린 유도체 |
| US8076352B2 (en) | 2004-03-15 | 2011-12-13 | Ptc Therapeutics, Inc. | Administration of carboline derivatives useful in the treatment of cancer and other diseases |
| US7767689B2 (en) | 2004-03-15 | 2010-08-03 | Ptc Therapeutics, Inc. | Carboline derivatives useful in the treatment of cancer |
| US20070015798A1 (en) * | 2005-02-25 | 2007-01-18 | Xun Li | Efficient and stereoselective process for large scale synthesis of (3R)-3-(2,3-dihydrobenzofuran-5-yl)-1,2,3,4-tetrahydropyrrolo[3,4-b]quinolin-9-one derivatives |
| JP2008531570A (ja) * | 2005-02-25 | 2008-08-14 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | ３−（ｒ）−３−（２，３−ジヒドロベンゾフラン−５−イル）−１，２，３，４−テトラヒドロピロロ［３，４−ｂ］キノリン−９−オンの有効かつ立体選択的大規模合成方法 |
| 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 |
| JP2009512711A (ja) | 2005-10-21 | 2009-03-26 | ブレインセルス，インコーポレイティド | Ｐｄｅ阻害による神経新生の調節 |
| EP1942879A1 (en) | 2005-10-31 | 2008-07-16 | Braincells, Inc. | Gaba receptor mediated modulation of neurogenesis |
| US20100216734A1 (en) | 2006-03-08 | 2010-08-26 | Braincells, Inc. | Modulation of neurogenesis by nootropic agents |
| EP2021000A2 (en) | 2006-05-09 | 2009-02-11 | Braincells, Inc. | Neurogenesis by modulating angiotensin |
| AU2007249435A1 (en) | 2006-05-09 | 2007-11-22 | Braincells, Inc. | 5 HT receptor mediated neurogenesis |
| AU2007292848A1 (en) | 2006-09-08 | 2008-03-13 | Braincells, Inc. | Combinations containing a 4-acylaminopyridine derivative |
| US20100184806A1 (en) | 2006-09-19 | 2010-07-22 | Braincells, Inc. | Modulation of neurogenesis by ppar agents |
| JP2012513464A (ja) | 2008-12-23 | 2012-06-14 | ザ トラスティーズ オブ コロンビア ユニヴァーシティ イン ザ シティ オブ ニューヨーク | ホスホジエステラーゼ阻害剤及びその使用 |
| WO2010099217A1 (en) | 2009-02-25 | 2010-09-02 | Braincells, Inc. | Modulation of neurogenesis using d-cycloserine combinations |
| RU2451686C1 (ru) * | 2010-12-27 | 2012-05-27 | Александр Васильевич Иващенко | ЗАМЕЩЕННЫЕ ГИДРИРОВАННЫЕ ТИЕНО-ПИРРОЛО [3,2-c] ПИРИДИНЫ, ЛИГАНДЫ, ФАРМАЦЕВТИЧЕСКАЯ КОМПОЗИЦИЯ И СПОСОБ ИХ ПРИМЕНЕНИЯ |
| KR101236188B1 (ko) * | 2011-03-10 | 2013-02-22 | 한국화학연구원 | 신규한 피롤로피리디논 유도체 및 그의 ｍｃｈ 수용체-1 관련 질환에 대한 치료학적 용도 |
| ES2632443T3 (es) | 2011-09-22 | 2017-09-13 | Viiv Healthcare Uk Limited | Compuestos de pirrolopiridinona y procedimientos de tratamiento del VIH |
| US20150119399A1 (en) | 2012-01-10 | 2015-04-30 | President And Fellows Of Harvard College | Beta-cell replication promoting compounds and methods of their use |
| JO3407B1 (ar) | 2012-05-31 | 2019-10-20 | Eisai R&D Man Co Ltd | مركبات رباعي هيدرو بيرازولو بيريميدين |
| US11427600B2 (en) | 2014-06-27 | 2022-08-30 | Nogra Pharma Limited | Aryl receptor modulators and methods of making and using the same |
| 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 |
| CN108752340B (zh) * | 2018-07-18 | 2020-09-01 | 山东中医药大学附属医院 | 吡咯并喹啉衍生物及其在治疗心律失常中的用途 |
| CN109134463B (zh) * | 2018-09-17 | 2020-05-08 | 山东大学 | β-咔啉类5型磷酸二酯酶抑制剂及其制备方法和用途 |
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| CA2213510A1 (en) | 1995-06-01 | 1996-12-05 | Takeda Chemical Industries, Ltd. | Diazepinones, their production and use |
| GB9514464D0 (en) * | 1995-07-14 | 1995-09-13 | Glaxo Lab Sa | Medicaments |
| US6248739B1 (en) | 1999-01-08 | 2001-06-19 | Pharmacia & Upjohn Company | Quinolinecarboxamides as antiviral agents |
| FR2792937B1 (fr) * | 1999-04-27 | 2001-08-10 | Cemaf | NOUVEAUX DERIVES DE PYRROLO-(3,4-b) QUINOLEINE, LEUR PROCEDE DE PREPARATION ET LEUR UTILISATION A TITRE DE MEDICAMENT |
| UA72611C2 (uk) | 2000-05-17 | 2005-03-15 | Орто-Макнейл Фармацевтикал, Інк. | Похідні заміщеного піролопіридинону, корисні як інгібітори фосфодіестерази |
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2001
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2004
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Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6043252A (en) * | 1997-05-05 | 2000-03-28 | Icos Corporation | Carboline derivatives |
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