EA016026B1 - 3-(1,3-бензодиоксол-5-ил)-6-(4-циклопропилпиперазин-1-ил)пиридазин, его соли и сольваты и его применение в качестве антагониста н3 рецептора гистамина - Google Patents
3-(1,3-бензодиоксол-5-ил)-6-(4-циклопропилпиперазин-1-ил)пиридазин, его соли и сольваты и его применение в качестве антагониста н3 рецептора гистамина Download PDFInfo
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- EA016026B1 EA016026B1 EA200870586A EA200870586A EA016026B1 EA 016026 B1 EA016026 B1 EA 016026B1 EA 200870586 A EA200870586 A EA 200870586A EA 200870586 A EA200870586 A EA 200870586A EA 016026 B1 EA016026 B1 EA 016026B1
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- Eurasian Patent Office
- Prior art keywords
- compound
- compounds
- histamine
- receptor
- treatment
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- IENZQIKPVFGBNW-UHFFFAOYSA-N prazosin Chemical compound N=1C(N)=C2C=C(OC)C(OC)=CC2=NC=1N(CC1)CCN1C(=O)C1=CC=CO1 IENZQIKPVFGBNW-UHFFFAOYSA-N 0.000 description 1
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- UNAANXDKBXWMLN-UHFFFAOYSA-N sibutramine Chemical compound C=1C=C(Cl)C=CC=1C1(C(N(C)C)CC(C)C)CCC1 UNAANXDKBXWMLN-UHFFFAOYSA-N 0.000 description 1
- IZTQOLKUZKXIRV-YRVFCXMDSA-N sincalide Chemical compound C([C@@H](C(=O)N[C@@H](CCSC)C(=O)NCC(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC=1C=CC=CC=1)C(N)=O)NC(=O)[C@@H](N)CC(O)=O)C1=CC=C(OS(O)(=O)=O)C=C1 IZTQOLKUZKXIRV-YRVFCXMDSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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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
- A61K31/50—Pyridazines; Hydrogenated pyridazines
- A61K31/501—Pyridazines; Hydrogenated pyridazines not condensed and containing further heterocyclic rings
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- A—HUMAN NECESSITIES
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- 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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Landscapes
- Health & Medical Sciences (AREA)
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- Bioinformatics & Cheminformatics (AREA)
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- Orthopedic Medicine & Surgery (AREA)
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- Physical Education & Sports Medicine (AREA)
- Otolaryngology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
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| PCT/EP2007/054940 WO2007137968A1 (en) | 2006-05-29 | 2007-05-22 | 3- (1, 3-benz0di0x0l-5-yl) -6- (4-cyclopropylpiperazin-1-yl) -pyridazine, its salts and solvates and its use as histamine h3 receptor antagonist |
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| EA200870586A1 EA200870586A1 (ru) | 2009-10-30 |
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| EP (2) | EP2402324A1 (enExample) |
| JP (1) | JP5694661B2 (enExample) |
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| AT (1) | ATE538116T1 (enExample) |
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Families Citing this family (15)
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| ES2375929T3 (es) * | 2005-07-04 | 2012-03-07 | High Point Pharmaceuticals, Llc | Antagonistas del receptor histamina h3. |
| WO2007009236A1 (en) * | 2005-07-20 | 2007-01-25 | Merck Frosst Canada Ltd. | Heteroaromatic compounds as inhibitors of stearoyl-coenzyme a delta-9 desaturase |
| AU2006326815A1 (en) * | 2005-12-20 | 2007-06-28 | Merck Frosst Canada Ltd. | Heteroaromatic compounds as inhibitors of stearoyl-coenzyme A delta-9 desaturase |
| CA2653062A1 (en) * | 2006-05-23 | 2007-11-29 | Transtech Pharma, Inc. | 6- (4-cyclopropylpiperazin-1-yl) -2 ' -methyl- [3, 4 ' ] -bipyridine and its use as a medicament |
| HRP20120227T1 (hr) | 2006-05-29 | 2012-04-30 | High Point Pharmaceuticals | 3-(1,3-benzodioksol-5-il)-6-(4-ciklopropilpiperazin-1-il)piridazin, njegove soli i solvati te njegova uporaba kao antagonista histaminskog h3 receptora |
| CN101472887A (zh) | 2006-06-23 | 2009-07-01 | 艾博特公司 | 作为组胺h3受体调节物的环丙胺衍生物 |
| US9108948B2 (en) | 2006-06-23 | 2015-08-18 | Abbvie Inc. | Cyclopropyl amine derivatives |
| EP2014656A3 (en) * | 2007-06-11 | 2011-08-24 | High Point Pharmaceuticals, LLC | New heteocyclic h3 antagonists |
| EP2025674A1 (de) | 2007-08-15 | 2009-02-18 | sanofi-aventis | Substituierte Tetrahydronaphthaline, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
| US9186353B2 (en) | 2009-04-27 | 2015-11-17 | Abbvie Inc. | Treatment of osteoarthritis pain |
| WO2012037258A1 (en) | 2010-09-16 | 2012-03-22 | Abbott Laboratories | Processes for preparing 1,2-substituted cyclopropyl derivatives |
| WO2013151982A1 (en) | 2012-04-03 | 2013-10-10 | Arena Pharmaceuticals, Inc. | Methods and compounds useful in treating pruritus, and methods for identifying such compounds |
| CN107428729B (zh) | 2015-02-09 | 2021-07-16 | 豪夫迈·罗氏有限公司 | 用于治疗癌症的化合物 |
| US12065433B2 (en) | 2018-10-24 | 2024-08-20 | Vanderbilt University | Positive allosteric modulators of the muscarinic acetylcholine receptor M1 |
| WO2022053541A1 (en) * | 2020-09-10 | 2022-03-17 | Eracal Therapeutics Ltd. | Compounds for use as appetite suppressant |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2003066604A2 (en) * | 2002-02-05 | 2003-08-14 | Novo Nordisk A/S | Novel aryl- and heteroarylpiperazines |
| WO2004054973A2 (en) * | 2002-12-18 | 2004-07-01 | Novo Nordisk A/S | Piperidine and pyrrolidine derivatives as antagonists of histamine h3 receptor |
Family Cites Families (109)
| Publication number | Priority date | Publication date | Assignee | Title |
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| GB753166A (en) | 1953-05-22 | 1956-07-18 | Miles Lab | Improvements in or relating to substituted piperazines |
| US2993899A (en) | 1958-03-31 | 1961-07-25 | Miles Lab | Acetylenically unsaturated piperazine derivatives |
| US3309370A (en) | 1964-07-16 | 1967-03-14 | Miles Lab | Bicycloalkyl piperazine derivatives and process |
| GB1293565A (en) | 1969-05-03 | 1972-10-18 | Aspro Nicholas Ltd | Aminophthalazines and pharmaceutical compositions thereof |
| US3886161A (en) | 1970-12-14 | 1975-05-27 | Sandoz Ag | 2-Piperazino-3-cyano-5-phenyl-pyridines |
| GB1345880A (en) | 1971-06-18 | 1974-02-06 | Cepbepe | Pyridazine derivatives |
| DE2516040C2 (de) | 1974-06-10 | 1984-12-20 | Dr. Karl Thomae Gmbh, 7950 Biberach | Benzimidazole, Verfahren zu deren Herstellung und diese enthaltende Arzneimittel |
| FR2306694A1 (fr) | 1975-04-07 | 1976-11-05 | Parcor | Derives de la piperazine |
| US3986161A (en) * | 1975-04-07 | 1976-10-12 | Sea-Scan, Inc. | Underwater directional guidance apparatus |
| GB1545094A (en) | 1976-12-14 | 1979-05-02 | Gist Brocades Nv | Piperazine derivatives |
| US4144346A (en) | 1977-01-31 | 1979-03-13 | Janssen Pharmaceutica N.V. | Novel 1-(1,3-dioxolan-2-ylmethyl)-1H-imidazoles |
| HU175471B (hu) | 1977-06-13 | 1980-08-28 | Gyogyszerkutato Intezet | Sposob poluchenija novykh proizvodnykh 3-skobka-1-pirazolil-skobka zakryta-piridazina |
| US4163849A (en) | 1978-03-17 | 1979-08-07 | Merck & Co., Inc. | Piperazinylpyrazines |
| DE2824764A1 (de) | 1978-06-06 | 1979-12-20 | Hoechst Ag | Neue pyridylpiperazinderivate und verfahren zu ihrer herstellung |
| EP0034752B1 (en) | 1980-02-22 | 1983-06-08 | Tanabe Seiyaku Co., Ltd. | Phenoxyalkane derivative and processes for preparing same |
| US4339579A (en) | 1980-12-29 | 1982-07-13 | American Home Products Corporation | 2,6-Bis-(pyrrolopyrazinyl)pyrazines |
| US4616014A (en) | 1981-10-22 | 1986-10-07 | Fujisawa Pharmaceutical Co., Ltd. | Triazine derivatives, and pharmaceutical compositions comprising the same |
| US5001125A (en) | 1984-03-26 | 1991-03-19 | Janssen Pharmaceutica N.V. | Anti-virally active pyridazinamines |
| FR2573075B1 (fr) | 1984-09-14 | 1987-03-20 | Innothera Lab Sa | Nouvelles (pyridyl-2)-1 piperazines, leur procede de preparation et leur application en therapeutique |
| JPS61267555A (ja) | 1984-11-27 | 1986-11-27 | Dainippon Pharmaceut Co Ltd | キノリン誘導体及びそれを有効成分とする抗潰瘍剤 |
| PH25772A (en) | 1985-08-30 | 1991-10-18 | Novo Industri As | Insulin analogues, process for their preparation |
| DK111387A (da) | 1986-03-05 | 1987-09-06 | Otsuka Pharma Co Ltd | Carbostyrilderivater og salte deraf, laegemiddel indeholdende saadanne derivater samt fremgangsmaade til fremstilling af derivaterne |
| DE3609596A1 (de) | 1986-03-21 | 1987-10-01 | Hoechst Ag | 2-azolylmethyl-2-aryl-1,3-dioxolane und deren salze, verfahren zu ihrer herstellung, sie enthaltende mittel und ihre verwendung |
| MY104343A (en) | 1987-11-23 | 1994-03-31 | Janssen Pharmaceutica Nv | Novel pyridizinamine deravatives |
| DE3803860A1 (de) | 1988-02-09 | 1989-08-17 | Basf Ag | N,n'-disubstituierte piperazine |
| DE3837825A1 (de) | 1988-11-08 | 1990-05-10 | Hoechst Ag | Neue insulinderivate, ihre verwendung und eine sie enthaltende pharmazeutische zubereitung |
| ES2058630T3 (es) | 1989-03-03 | 1994-11-01 | Dainippon Pharmaceutical Co | Derivados de 2-(1-piperazinil)-4-fenilcicloalcanopiridinas, procedimientos de preparacion y composiciones farmaceuticas que los contienen. |
| GB9012316D0 (en) | 1990-06-01 | 1990-07-18 | Wellcome Found | Pharmacologically active cns compounds |
| JPH08504798A (ja) | 1992-12-18 | 1996-05-21 | ザ ウエルカム ファウンデーション リミテッド | 酵素阻害薬としての，ピリミジン，ピリジン，プテリジノンおよびインダゾール誘導体 |
| WO1994022846A1 (en) | 1993-03-30 | 1994-10-13 | Pfizer Inc. | Compounds enhancing antitumor activity of other cytotoxic agents |
| WO1995000550A1 (en) | 1993-06-21 | 1995-01-05 | Novo Nordisk A/S | Aspb28 insulin crystals |
| BR9407508A (pt) | 1993-09-17 | 1997-01-07 | Novo Nordisk As | Derivado de insulina composição farmaceutica e processo para o tratamento de diabete em um paciente com necessidade deste tratamento |
| IL111730A (en) | 1993-11-29 | 1998-12-06 | Fujisawa Pharmaceutical Co | Piperazine derivatives processes for the preparation thereof and pharmaceutical compositions containing the same |
| US5504188A (en) | 1994-06-16 | 1996-04-02 | Eli Lilly And Company | Preparation of stable zinc insulin analog crystals |
| AU6318896A (en) | 1995-07-06 | 1997-02-05 | Japan Tobacco Inc. | Benzamidoxime derivatives and medicinal use thereof |
| US6130217A (en) | 1995-09-20 | 2000-10-10 | Pfizer Inc | Compounds enhancing antitumor activity of other cytotoxic agents |
| BR9611311A (pt) | 1995-11-09 | 1999-06-29 | Synthelabo | Derivados de 5-fenil-3-(piperidin-4-il)-1,3,4-oxadiazol-2(3h)-ona úteis como ligantes dos receptores 5-ht4 ou h3 |
| WO1997026265A1 (en) | 1996-01-17 | 1997-07-24 | Novo Nordisk A/S | Fused 1,2,4-thiadiazine and fused 1,4-thiazine derivatives, their preparation and use |
| EP0923580A1 (en) | 1996-07-26 | 1999-06-23 | Dr. Reddy's Research Foundation | Thiazolidinedione compounds having antidiabetic, hypolipidaemic, antihypertensive properties, process for their preparation and pharmaceutical compositions thereof |
| JP3149958B2 (ja) | 1996-08-30 | 2001-03-26 | ノボ ノルディスク アクティーゼルスカブ | Ｇｌｐ―１誘導体 |
| DZ2376A1 (fr) | 1996-12-19 | 2002-12-28 | Smithkline Beecham Plc | Dérivés de sulfonamides nouveaux procédé pour leurpréparation et compositions pharmaceutiques les c ontenant. |
| PT958296E (pt) | 1996-12-31 | 2003-11-28 | Reddys Lab Ltd Dr | Compostos heterociclicos processo para a sua preparacao composicoes farmaceuticas contendo-os e sua utilizacao no tratamento da diabetes e doencas relacionadas |
| WO1997041119A1 (en) | 1997-05-02 | 1997-11-06 | Dr. Reddy's Research Foundation | Novel antidiabetic compounds having hypolipidaemic, antihypertensive properties, process for their preparation and pharmaceutical compositions containing them |
| JP2003514508A (ja) | 1997-07-01 | 2003-04-15 | ノボ ノルディスク アクティーゼルスカブ | グルカゴン拮抗剤／逆作用剤 |
| US6613942B1 (en) | 1997-07-01 | 2003-09-02 | Novo Nordisk A/S | Glucagon antagonists/inverse agonists |
| KR20010021936A (ko) | 1997-07-16 | 2001-03-15 | 한센 핀 베네드, 안네 제헤르, 웨이콥 마리안느 | 융합된 1,2,4-티아디아진 유도체, 그의 제조와 사용 |
| EP1020445B1 (en) | 1997-10-02 | 2008-08-13 | Eisai R&D Management Co., Ltd. | Fused pyridine derivatives |
| WO1999019313A1 (en) | 1997-10-27 | 1999-04-22 | Dr. Reddy's Research Foundation | Novel tricyclic compounds and their use in medicine; process for their preparation and pharmaceutical compositions containing them |
| US6440961B1 (en) | 1997-10-27 | 2002-08-27 | Dr. Reddy's Research Foundation | Tricyclic compounds and their use in medicine: process for their preparation and pharmaceutical compositions containing them |
| SI20324A (sl) | 1997-10-27 | 2001-02-28 | Agouron Pharmaceuticals, Inc. | Substituirane 4-amino-tiazol-2-il spojine kot cdk inhibitorji |
| DE69803750T2 (de) | 1997-12-02 | 2002-09-12 | Dr. Reddy's Research Foundation, Andhra Pradesh | Thiazolidinedione- und oxazolidinedione-derivate mit antidiabetischen, hypolipidämischen und anti hypertensiven eigenschaften |
| GB9803536D0 (en) | 1998-02-19 | 1998-04-15 | Black James Foundation | Histamine H,receptor ligands |
| EP0978512A1 (en) | 1998-07-29 | 2000-02-09 | Societe Civile Bioprojet | Non-imidazole aryloxy (or arylthio) alkylamines as histamine H3-receptor antagonists and their therapeutic applications |
| EP1123267A1 (en) | 1998-10-21 | 2001-08-16 | Novo Nordisk A/S | New compounds, their preparation and use |
| EP1123292A1 (en) | 1998-10-21 | 2001-08-16 | Novo Nordisk A/S | New compounds, their preparation and use |
| EP1123269A1 (en) | 1998-10-21 | 2001-08-16 | Novo Nordisk A/S | New compounds, their preparation and use |
| JP2002527520A (ja) | 1998-10-21 | 2002-08-27 | ノボ ノルディスク アクティーゼルスカブ | 新規化合物、その製造及び使用 |
| EP1123268A1 (en) | 1998-10-21 | 2001-08-16 | Novo Nordisk A/S | New compounds, their preparation and use |
| WO2000023425A1 (en) | 1998-10-21 | 2000-04-27 | Novo Nordisk A/S | New compounds, their preparation and use |
| DE69908648T2 (de) | 1998-12-18 | 2004-05-13 | Novo Nordisk A/S | Kondensierte 1,2,4-thiadiazinderivate, ihre herstellung und verwendung |
| WO2000041121A1 (en) | 1999-01-07 | 2000-07-13 | Ccrewards.Com | Method and arrangement for issuance and management of digital coupons and sales offers |
| EP1147094A1 (en) | 1999-01-15 | 2001-10-24 | Novo Nordisk A/S | Non-peptide glp-1 agonists |
| PL351492A1 (en) | 1999-04-16 | 2003-04-22 | Reddys Lab Ltd Dr | Novel polymorphic forms of an antidiabetic agent: process for their preparation and pharmaceutical compositions containing them |
| WO2000063191A1 (en) | 1999-04-16 | 2000-10-26 | Dr. Reddy's Research Foundation | Novel polymorphic forms of an antidiabetic agent: process for their preparation and a pharmaceutical composition containing them |
| AU4465200A (en) | 1999-04-16 | 2000-11-02 | Dr. Reddy's Research Foundation | Novel polymorphic forms of an antidiabetic agent: process for their preparation and a pharmaceutical composition containing them |
| WO2000063196A1 (en) | 1999-04-20 | 2000-10-26 | Novo Nordisk A/S | New compounds, their preparation and use |
| JP2002542237A (ja) | 1999-04-20 | 2002-12-10 | ノボ ノルディスク アクティーゼルスカブ | 新規な化合物、それらの製造及び使用 |
| BR0009864A (pt) | 1999-04-20 | 2002-01-08 | Novo Nordisk As | Composto, composição farmacêutica, métodos para o tratamento de doenças, para o tratamento e/ou prevenção de condições mediadas pelos receptores nucleares e para o tratamento e/ou prevenção de diabete e/ou obesidade, e, uso de um composto |
| AU3958100A (en) | 1999-04-20 | 2000-11-02 | Novo Nordisk A/S | New compounds, their preparation and use |
| AU2935200A (en) | 1999-04-30 | 2000-11-17 | Pfizer Products Inc. | Compounds for the treatment of obesity |
| GB9926302D0 (en) | 1999-11-05 | 2000-01-12 | Smithkline Beecham Plc | Novel compounds |
| GB9926303D0 (en) | 1999-11-05 | 2000-01-12 | Smithkline Beecham Plc | Novel compounds |
| US6602872B1 (en) | 1999-12-13 | 2003-08-05 | Merck & Co., Inc. | Substituted pyridazines having cytokine inhibitory activity |
| FR2802206B1 (fr) | 1999-12-14 | 2005-04-22 | Sod Conseils Rech Applic | Derives de 4-aminopiperidine et leur utilisation en tant que medicament |
| CZ20022100A3 (cs) | 1999-12-16 | 2002-09-11 | Schering Corporation | Substituované imidazolové deriváty a farmaceutický prostředek |
| FI20000480A0 (fi) | 2000-03-01 | 2000-03-01 | Orion Yhtymae Oyj | Kinoliini- ja naftaleenijohdannaisia alfa-2 antagonisteina |
| WO2001066534A2 (en) | 2000-03-09 | 2001-09-13 | Abbott Laboratories | Cyclic and bicyclic diamino histamine-3 receptor antagonists |
| ES2213693T3 (es) | 2000-03-31 | 2004-09-01 | Ortho-Mcneil Pharmaceutical, Inc. | Derivados de indolizina fenil-sustituidos y su uso como ligandos del receptor h3 de la histamina. |
| EP1268478B1 (en) | 2000-03-31 | 2007-05-02 | Ortho-McNeil Pharmaceutical, Inc. | Phenyl-substituted imidazopyridines |
| WO2001074810A2 (en) | 2000-03-31 | 2001-10-11 | Ortho Mcneil Pharmaceutical, Inc. | Method for using 2-aryloxyalkylaminobenzoxazoles and 2-aryloxyalkylaminobenzothiazoles as h3 antagonists |
| AU2001247906A1 (en) | 2000-03-31 | 2001-10-15 | Ortho-Mcneil Pharmaceutical, Inc. | Phenyl-substituted indoles and indazoles |
| AU2001249672A1 (en) | 2000-03-31 | 2001-10-15 | Ortho-Mcneil Pharmaceutical, Inc. | Method for using 2- or 3-aryl substituted imidazo(1,2-a) pyridines as h3 antagonists |
| PL360373A1 (en) | 2000-08-08 | 2004-09-06 | Ortho Mcneil Pharmaceutical, Inc. | Non-imidazole aryloxypiperidines as h3 receptor ligands |
| US6316475B1 (en) | 2000-11-17 | 2001-11-13 | Abbott Laboratories | Aminoalkoxybiphenylcarboxamides as histamine-3 receptor ligands and their therapeutic applications |
| US20030078271A1 (en) | 2001-01-31 | 2003-04-24 | Blackburn Thomas P. | Use of GAL3 receptor antagonists for the treatment of depression and/or anxiety and compounds useful in such methods |
| US20030073672A1 (en) | 2001-09-05 | 2003-04-17 | Breitenbucher J. Guy | Method for treating allergies using substituted pyrazoles |
| US20030236259A1 (en) | 2002-02-05 | 2003-12-25 | Rolf Hohlweg | Novel aryl- and heteroarylpiperazines |
| US6864261B2 (en) | 2002-05-02 | 2005-03-08 | Euro-Celtique S.A. | Therapeutic agents useful for treating pain |
| SE0201544D0 (sv) | 2002-05-17 | 2002-05-17 | Biovitrum Ab | Novel compounds and thier use |
| ES2283768T3 (es) | 2002-06-06 | 2007-11-01 | Novo Nordisk A/S | Hexahidropirrolo(1,2-a)piracinas, octahidropirido(1,2-a)piracinas y decahidropiracino(1,2-a)acepinas sustituidas. |
| US6906060B2 (en) | 2002-06-06 | 2005-06-14 | Novo Nordisk A/S | Substituted hexahydropyrrolo[1,2-a]pyrazines, octahydropyrido[1,2-a]-pyrazines and decahydropyrazino[1,2-a]azepines |
| DK1651615T3 (da) | 2003-07-29 | 2010-05-25 | High Point Pharmaceuticals Llc | Pyridazinyl-piperaziner og anvendelse deraf som histamin-H3-receptorligander |
| CA2551037A1 (en) | 2003-09-22 | 2005-03-31 | Banyu Pharmaceutical Co., Ltd. | Novel piperidine derivative |
| FR2864080B1 (fr) | 2003-12-23 | 2006-02-03 | Sanofi Synthelabo | Derives de 1-piperazine-et-1-homopiperazine-carboxylates, leur preparation et leur application en therapeutique |
| ATE499364T1 (de) | 2004-04-09 | 2011-03-15 | Merck Sharp & Dohme | Hemmer der akt aktivität |
| JP5221952B2 (ja) | 2004-05-08 | 2013-06-26 | ノバルティス・インターナショナル・ファーマシューティカル・リミテッド | ３−アリール−５，６−ジ置換ピリダジン類 |
| MX2007005247A (es) | 2004-11-02 | 2008-03-13 | Univ Northwestern | Compuestos de piridazina, composiciones y metodos. |
| ATE466842T1 (de) | 2004-12-03 | 2010-05-15 | Hoffmann La Roche | 3-substituierte pyridinderivate als h3- antagonisten |
| GB0501146D0 (en) | 2005-01-20 | 2005-02-23 | Astrazeneca Ab | Novel benzamide derivatives |
| CA2606288A1 (en) | 2005-04-18 | 2006-10-26 | Neurogen Corporation | Subtituted heteroaryl cb1 antagonists |
| FR2885615B1 (fr) | 2005-05-12 | 2007-06-22 | Servier Lab | Nouveaux derives de phenylpyridinylpiperazine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| FR2885616B1 (fr) | 2005-05-12 | 2007-06-22 | Servier Lab | Nouveaux derives de phenylpyridinylpiperazine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| ES2375929T3 (es) | 2005-07-04 | 2012-03-07 | High Point Pharmaceuticals, Llc | Antagonistas del receptor histamina h3. |
| US7956050B2 (en) | 2005-07-15 | 2011-06-07 | Albany Molecular Research, Inc. | Aryl- and heteroaryl-substituted tetrahydrobenzazepines and use thereof to block reuptake of norepinephrine, dopamine, and serotonin |
| JP2009506987A (ja) | 2005-08-02 | 2009-02-19 | ニューロゲン コーポレイション | ジピペラジニルケトンおよび関連する類似体 |
| JP2009531376A (ja) | 2006-03-28 | 2009-09-03 | ハイ ポイント ファーマシューティカルズ，リミティド ライアビリティ カンパニー | ヒスタミンｈ３受容体活性を有するベンゾチアゾール |
| CA2653062A1 (en) | 2006-05-23 | 2007-11-29 | Transtech Pharma, Inc. | 6- (4-cyclopropylpiperazin-1-yl) -2 ' -methyl- [3, 4 ' ] -bipyridine and its use as a medicament |
| HRP20120227T1 (hr) | 2006-05-29 | 2012-04-30 | High Point Pharmaceuticals | 3-(1,3-benzodioksol-5-il)-6-(4-ciklopropilpiperazin-1-il)piridazin, njegove soli i solvati te njegova uporaba kao antagonista histaminskog h3 receptora |
| EP2014656A3 (en) | 2007-06-11 | 2011-08-24 | High Point Pharmaceuticals, LLC | New heteocyclic h3 antagonists |
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003066604A2 (en) * | 2002-02-05 | 2003-08-14 | Novo Nordisk A/S | Novel aryl- and heteroarylpiperazines |
| WO2004054973A2 (en) * | 2002-12-18 | 2004-07-01 | Novo Nordisk A/S | Piperidine and pyrrolidine derivatives as antagonists of histamine h3 receptor |
Also Published As
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| EP2079732B1 (en) | 2011-12-21 |
| WO2007137968A1 (en) | 2007-12-06 |
| EP2079732B9 (en) | 2012-03-21 |
| ES2375872T9 (es) | 2012-07-19 |
| RS52234B (sr) | 2012-10-31 |
| ATE538116T1 (de) | 2012-01-15 |
| SG163547A1 (en) | 2010-08-30 |
| IL194681A (en) | 2013-09-30 |
| ZA200808730B (en) | 2010-02-24 |
| EP2079732A1 (en) | 2009-07-22 |
| US8378097B2 (en) | 2013-02-19 |
| EP2402324A1 (en) | 2012-01-04 |
| PT2079732E (pt) | 2012-02-02 |
| JP5694661B2 (ja) | 2015-04-01 |
| AU2007267197A1 (en) | 2007-12-06 |
| HRP20120227T1 (hr) | 2012-04-30 |
| US20090176793A1 (en) | 2009-07-09 |
| SI2079732T1 (sl) | 2012-03-30 |
| BRPI0711370A2 (pt) | 2011-11-01 |
| PL2079732T3 (pl) | 2012-05-31 |
| CA2659570A1 (en) | 2007-12-06 |
| AU2007267197B2 (en) | 2011-12-01 |
| ES2375872T3 (es) | 2012-03-07 |
| KR20090040259A (ko) | 2009-04-23 |
| DK2079732T3 (da) | 2012-01-23 |
| CY1112455T1 (el) | 2015-12-09 |
| CN102295606A (zh) | 2011-12-28 |
| JP2009538861A (ja) | 2009-11-12 |
| MX2008014766A (es) | 2009-03-06 |
| CA2659570C (en) | 2015-10-06 |
| NZ571972A (en) | 2011-09-30 |
| CN101460487A (zh) | 2009-06-17 |
| EA200870586A1 (ru) | 2009-10-30 |
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