AU733967B2 - Use of 1-benzyl-3-(substituted hetaryl)-fused pyrazole derivatives for the treatment of specific disorders of the cardiovascular system and of the central nervous system - Google Patents
Use of 1-benzyl-3-(substituted hetaryl)-fused pyrazole derivatives for the treatment of specific disorders of the cardiovascular system and of the central nervous system Download PDFInfo
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- AU733967B2 AU733967B2 AU50494/98A AU5049498A AU733967B2 AU 733967 B2 AU733967 B2 AU 733967B2 AU 50494/98 A AU50494/98 A AU 50494/98A AU 5049498 A AU5049498 A AU 5049498A AU 733967 B2 AU733967 B2 AU 733967B2
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- Australia
- Prior art keywords
- indazole
- hydroxymethylfuran
- compounds
- treatment
- general formula
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- 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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- 229960004027 molsidomine Drugs 0.000 description 1
- YZMHQCWXYHARLS-UHFFFAOYSA-N naphthalene-1,2-disulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(S(=O)(=O)O)=CC=C21 YZMHQCWXYHARLS-UHFFFAOYSA-N 0.000 description 1
- 239000002840 nitric oxide donor Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 235000019701 semiluxury food Nutrition 0.000 description 1
- 231100000872 sexual dysfunction Toxicity 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
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- 208000019116 sleep disease Diseases 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
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- 239000000725 suspension Substances 0.000 description 1
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- 230000002792 vascular Effects 0.000 description 1
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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
-
- 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
- A61K31/415—1,2-Diazoles
- A61K31/416—1,2-Diazoles condensed with carbocyclic ring systems, e.g. indazole
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
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- 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
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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
-
- 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
- A61P9/08—Vasodilators for multiple indications
-
- 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)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Epidemiology (AREA)
- Neurology (AREA)
- Hospice & Palliative Care (AREA)
- Biomedical Technology (AREA)
- Vascular Medicine (AREA)
- Neurosurgery (AREA)
- Urology & Nephrology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19642255A DE19642255A1 (de) | 1996-10-14 | 1996-10-14 | Verwendung von 1-Benzyl-3-(substituierten-hetaryl) -kondensierten Pyrazol-Derivaten |
| DE19642255 | 1996-10-14 | ||
| PCT/EP1997/005381 WO1998016223A1 (de) | 1996-10-14 | 1997-10-01 | Verwendung von 1-benzyl-3-(substituiertes-hetaryl)-kondensierten pyrazol-derivaten zur belandlung von speziellen erkrankungen des herz-kreislaufsystems und des zentralnervensystems |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU5049498A AU5049498A (en) | 1998-05-11 |
| AU733967B2 true AU733967B2 (en) | 2001-05-31 |
Family
ID=7808650
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU50494/98A Ceased AU733967B2 (en) | 1996-10-14 | 1997-10-01 | Use of 1-benzyl-3-(substituted hetaryl)-fused pyrazole derivatives for the treatment of specific disorders of the cardiovascular system and of the central nervous system |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US6180656B1 (https=) |
| EP (1) | EP0932403B1 (https=) |
| JP (2) | JP2001502318A (https=) |
| AT (1) | ATE311184T1 (https=) |
| AU (1) | AU733967B2 (https=) |
| BR (1) | BR9712304A (https=) |
| CA (1) | CA2268314C (https=) |
| CZ (1) | CZ129299A3 (https=) |
| DE (2) | DE19642255A1 (https=) |
| EE (1) | EE9900156A (https=) |
| ES (1) | ES2252777T3 (https=) |
| HU (1) | HUP9903885A3 (https=) |
| ID (1) | ID22162A (https=) |
| IL (1) | IL129318A (https=) |
| NO (1) | NO991685L (https=) |
| NZ (1) | NZ335091A (https=) |
| PL (1) | PL332719A1 (https=) |
| SK (1) | SK46599A3 (https=) |
| TR (1) | TR199900782T2 (https=) |
| TW (1) | TW442482B (https=) |
| WO (1) | WO1998016223A1 (https=) |
Families Citing this family (119)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19744026A1 (de) | 1997-10-06 | 1999-04-08 | Hoechst Marion Roussel De Gmbh | Pyrazol-Derivate, ihre Herstellung und ihre Verwendung in Arzneimitteln |
| DE19846514A1 (de) * | 1998-10-09 | 2000-04-20 | Bayer Ag | Neue Heterocyclyl-methyl-substituierte Pyrazole |
| DE19853278A1 (de) | 1998-11-19 | 2000-05-25 | Aventis Pharma Gmbh | Substituierte 4-Amino-2-aryl-cyclopenta[d]pyrimidine, ihre Herstellung, ihre Verwendung und sie enthaltende pharmazeutische Präparate |
| DE19904710A1 (de) | 1999-02-05 | 2000-08-10 | Aventis Pharma Gmbh | Substituierte 4-Amino-2-aryl-tetrahydrochinazoline, ihre Herstellung, ihre Verwendung und sie enthaltende pharmazeutische Präparate |
| DE19943634A1 (de) | 1999-09-13 | 2001-04-12 | Bayer Ag | Neuartige Dicarbonsäurederivate mit pharmazeutischen Eigenschaften |
| DE19943636A1 (de) | 1999-09-13 | 2001-03-15 | Bayer Ag | Neuartige Dicarbonsäurederivate mit pharmazeutischen Eigenschaften |
| DE19943635A1 (de) | 1999-09-13 | 2001-03-15 | Bayer Ag | Neuartige Aminodicarbonsäurederivate mit pharmazeutischen Eigenschaften |
| GB0002666D0 (en) * | 2000-02-04 | 2000-03-29 | Univ London | Blockade of voltage dependent sodium channels |
| DE10021069A1 (de) * | 2000-04-28 | 2001-10-31 | Bayer Ag | Substituiertes Pyrazolderivat |
| US6387942B2 (en) * | 2000-06-19 | 2002-05-14 | Yung Shin Pharmaceutical Ind. Co. Ltd | Method of treating disorders related to protease-activated receptors-induced cell activation |
| KR20050117594A (ko) * | 2000-06-23 | 2005-12-15 | 주식회사 하이닉스반도체 | 반도체 소자의 제조 방법 |
| KR20020001013A (ko) * | 2000-06-23 | 2002-01-09 | 리팡유 | 트롬빈-유도 혈소판 응집 저해방법 |
| DE10054278A1 (de) * | 2000-11-02 | 2002-05-08 | Bayer Ag | Verwendung von Stimulatoren der löslichen Guanylatcyclase zur Behandlung von Osteoporose |
| ES2231581T3 (es) | 2000-11-22 | 2005-05-16 | Bayer Healthcare Ag | Nuevos derivados de pirazolopiridina sustituidos con lactama. |
| AR031176A1 (es) | 2000-11-22 | 2003-09-10 | Bayer Ag | Nuevos derivados de pirazolpiridina sustituidos con piridina |
| DE10057751A1 (de) | 2000-11-22 | 2002-05-23 | Bayer Ag | Neue Carbamat-substituierte Pyrazolopyridinderivate |
| DE10057754A1 (de) | 2000-11-22 | 2002-05-23 | Bayer Ag | Neue Sulfonamid-substituierte Pyrazolopyridinderivate |
| DE60201921T2 (de) | 2001-01-24 | 2005-10-06 | Yung Shin Pharmaceutical Ind. Co., Ltd. | Kondensierte Pyrazolverbindungen |
| DE10109859A1 (de) | 2001-03-01 | 2002-09-05 | Bayer Ag | Neuartige Aminodicarbonsäurederivate |
| DE10109858A1 (de) * | 2001-03-01 | 2002-09-05 | Bayer Ag | Neuartige halogensubstituierte Aminodicarbonsäurederivate |
| DE10109861A1 (de) | 2001-03-01 | 2002-09-05 | Bayer Ag | Neuartige seitenkettenhalogenierte Aminodicarbonsäurederivate |
| DE10122894A1 (de) * | 2001-05-11 | 2002-11-14 | Bayer Ag | Neue Sulfonat-substituierte Pyrazolopyridinderivate |
| US7049334B2 (en) * | 2001-09-14 | 2006-05-23 | Carlsbad Technology, Inc. | Enhancement of learning and memory and treatment of amnesia |
| US20040077702A1 (en) * | 2001-09-14 | 2004-04-22 | Wen-Mei Fu | Treatment of nuerodegenerative diseases |
| TWI264304B (en) | 2002-01-25 | 2006-10-21 | Yung Shin Pharm Ind Co Ltd | Methods of treating sepsis |
| DE10220570A1 (de) | 2002-05-08 | 2003-11-20 | Bayer Ag | Carbamat-substituierte Pyrazolopyridine |
| JP4499721B2 (ja) * | 2003-06-30 | 2010-07-07 | ヒフ バイオ，インク． | 化合物、組成物および方法 |
| JP2005089457A (ja) * | 2003-09-03 | 2005-04-07 | Yung Shin Pharmaceutical Industry Co Ltd | 骨成長を促進するまたは骨吸収を阻害するための薬剤組成物 |
| WO2005077005A2 (en) * | 2004-02-04 | 2005-08-25 | The General Hospital Corporation | Enhancing the effectiveness of an inhaled therapeutic gas |
| DE102005050376A1 (de) * | 2005-10-21 | 2007-05-31 | Bayer Healthcare Ag | Dicarbonsäure-Derivate und ihre Verwendung |
| DE102005050377A1 (de) * | 2005-10-21 | 2007-04-26 | Bayer Healthcare Ag | Heterocyclische Verbindungen und ihre Verwendung |
| DE102005050498A1 (de) * | 2005-10-21 | 2007-06-06 | Bayer Healthcare Aktiengesellschaft | Cyclopropylessigsäure-Derivate und ihre Verwendung |
| DE102005050375A1 (de) * | 2005-10-21 | 2007-04-26 | Bayer Healthcare Ag | Tetrazol-Derivate und ihre Verwendung |
| DE102005050497A1 (de) * | 2005-10-21 | 2007-04-26 | Bayer Healthcare Ag | Difluorphenol-Derivate und ihre Verwendung |
| DE102006020327A1 (de) * | 2006-04-27 | 2007-12-27 | Bayer Healthcare Ag | Heterocyclisch substituierte, anellierte Pyrazol-Derivate und ihre Verwendung |
| DE102006021733A1 (de) * | 2006-05-09 | 2007-11-22 | Bayer Healthcare Ag | 3-Tetrazolylindazole und 3-Tetrazolylpyrazolopyridine sowie ihre Verwendung |
| DE102006043443A1 (de) * | 2006-09-15 | 2008-03-27 | Bayer Healthcare Ag | Neue aza-bicyclische Verbindungen und ihre Verwendung |
| DE102006054757A1 (de) * | 2006-11-21 | 2008-05-29 | Bayer Healthcare Ag | Neue aza-bicyclische Verbindungen und ihre Verwendung |
| DE102007015034A1 (de) * | 2007-03-29 | 2008-10-02 | Bayer Healthcare Ag | Lactam-substituierte Dicarbonsäuren und ihre Verwendung |
| DE102007015035A1 (de) * | 2007-03-29 | 2008-10-02 | Bayer Healthcare Ag | Substituierte Dibenzoesäure-Derivate und ihre Verwendung |
| US20100144864A1 (en) * | 2007-04-05 | 2010-06-10 | Ironwood Pharmaceuticals, Inc. | Soluble guanylate cyclase (sgc) modulators for treatment of lipid related disorders |
| US20080252028A1 (en) * | 2007-04-16 | 2008-10-16 | Ming-Tai Huang | Shock absorbing device for toy stroller |
| DE102007026392A1 (de) | 2007-06-06 | 2008-12-11 | Bayer Healthcare Ag | Lösungen für die Perfusion und Konservierung von Organen und Geweben |
| DE102007028320A1 (de) | 2007-06-20 | 2008-12-24 | Bayer Healthcare Ag | Substituierte Oxazolidinone und ihre Verwendung |
| DE102007028407A1 (de) | 2007-06-20 | 2008-12-24 | Bayer Healthcare Ag | Substituierte Oxazolidinone und ihre Verwendung |
| DE102007028319A1 (de) | 2007-06-20 | 2008-12-24 | Bayer Healthcare Ag | Substituierte Oxazolidinone und ihre Verwendung |
| DE102007028406A1 (de) | 2007-06-20 | 2008-12-24 | Bayer Healthcare Ag | Substituierte Oxazolidinone und ihre Verwendung |
| EP2138178A1 (en) | 2008-06-28 | 2009-12-30 | Bayer Schering Pharma Aktiengesellschaft | Oxazolidninones for the treatment fo chronic obstructive pulmonary disease (COPD) and/or asthma |
| DE102008063992A1 (de) | 2008-12-19 | 2010-09-02 | Lerner, Zinoviy, Dipl.-Ing. | Neue aliphatisch substituierte Pyrazolopyridine und ihre Verwendung |
| DE102009004245A1 (de) | 2009-01-09 | 2010-07-15 | Bayer Schering Pharma Aktiengesellschaft | Neue anellierte, Heteroatom-verbrückte Pyrazol- und Imidazol-Derivate und ihre Verwendung |
| PL2604608T3 (pl) * | 2009-11-27 | 2016-02-29 | Adverio Pharma Gmbh | Sposób wytwarzania {4,6-diamino-2-[1-(2-fluorobenzylo)-1H-pirazolo[3,4-b]pirydyn-3-ylo]pirymidyn-5-ylo}metylokarbaminianu metylu |
| UY33041A (es) | 2009-11-27 | 2011-06-30 | Bayer Schering Pharma Aktienegesellschaft | Procedimiento para la preparaciòn de {4,6-diamino-2-[1-(2-fluorobencil)-1h-pirazolo[3,4-b]piridin-3-il]pirimidin-5-il}carbamato de metilo y su purificaciòn para el uso como principio activo farmacèutico |
| DE102010021637A1 (de) | 2010-05-26 | 2011-12-01 | Bayer Schering Pharma Aktiengesellschaft | Substituierte 5-Fluor-1H-Pyrazolopyridine und ihre Verwendung |
| HRP20150987T1 (hr) * | 2010-05-26 | 2015-10-23 | Adverio Pharma Gmbh | UPORABA sGC STIMULATORA, sGC AKTIVATORA, SAMOSTALNO I U KOMBINACIJAMA S INHIBITORIMA PDE5 ZA LIJEÄŚENJE SISTEMSKE SKLEROZE (SSc) |
| EP2687210A1 (de) | 2010-06-25 | 2014-01-22 | Bayer Intellectual Property GmbH | Verwendung von Stimulatoren und Aktivatoren der löslichen Guanylatzyklase zur Behandlung von Sichelzellanämie und Konservierung von Blutersatzstoffen |
| EA201390060A1 (ru) | 2010-07-09 | 2013-07-30 | Байер Интеллектуэль Проперти Гмбх | Аннелированные пиримидины и триазины и их применение для лечения и/или профилактики сердечно-сосудистых заболеваний |
| DE102011003315A1 (de) | 2011-01-28 | 2012-08-02 | Bayer Schering Pharma Aktiengesellschaft | Annellierte Pyrimindine und Triazine und ihre Verwendung |
| DE102011007891A1 (de) | 2011-04-21 | 2012-10-25 | Bayer Pharma Aktiengesellschaft | Annellierte 4-Aminopyrimidine und ihre Verwendung |
| CN103180327B (zh) | 2010-07-09 | 2016-08-10 | 拜耳知识产权有限责任公司 | 稠环的4-氨基嘧啶及其作为可溶性鸟甘酸环化酶的刺激物的用途 |
| DE102010031149A1 (de) | 2010-07-09 | 2012-01-12 | Bayer Schering Pharma Aktiengesellschaft | Annellierte Pyrimidine und Triazine und ihre Verwendung |
| DE102010031148A1 (de) | 2010-07-09 | 2012-01-12 | Bayer Schering Pharma Ag | Annellierte 4-Aminopyrimidine und ihre Verwendung |
| DE102010031665A1 (de) | 2010-07-22 | 2012-01-26 | Bayer Schering Pharma Aktiengesellschaft | Substituierte Oxazolidinone und Oxazinanone und ihre Verwendung |
| DE102010031666A1 (de) | 2010-07-22 | 2012-01-26 | Bayer Schering Pharma Aktiengesellschaft | Carbamat-substituierte Diaminopyrimidine und ihre Verwendung |
| DE102010031667A1 (de) | 2010-07-22 | 2012-01-26 | Bayer Schering Pharma Aktiengesellschaft | Substituierte Methyl-pyrimidin-5-ylcarbamate und ihre Verwendung |
| DE102010040233A1 (de) | 2010-09-03 | 2012-03-08 | Bayer Schering Pharma Aktiengesellschaft | Bicyclische Aza-Heterocyclen und ihre Verwendung |
| DE102010043380A1 (de) | 2010-11-04 | 2012-05-10 | Bayer Schering Pharma Aktiengesellschaft | Benzyl-substituierte Carbamate und ihre Verwendung |
| DE102010043379A1 (de) | 2010-11-04 | 2012-05-10 | Bayer Schering Pharma Aktiengesellschaft | Substituierte 6-Fluor-1H-Pyrazolo[4,3-b]pyridine und ihre Verwendung |
| DE102011075399A1 (de) | 2011-05-06 | 2012-11-08 | Bayer Pharma Aktiengesellschaft | Substituierte Imidazopyridine und Imidazopyridazine und ihre Verwendung |
| DE102012200356A1 (de) | 2012-01-11 | 2013-07-11 | Bayer Intellectual Property Gmbh | Substituierte Imidazopyridine und Imidazopyridazine und ihre Verwendung |
| DE102011007890A1 (de) | 2011-04-21 | 2012-10-25 | Bayer Pharma Aktiengesellschaft | Fluoralkyl-substituierte Pyrazolopyridine und ihre Verwendung |
| JP6005134B2 (ja) | 2011-04-21 | 2016-10-12 | バイエル・インテレクチュアル・プロパティ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツングＢａｙｅｒ Ｉｎｔｅｌｌｅｃｔｕａｌ Ｐｒｏｐｅｒｔｙ ＧｍｂＨ | フルオロアルキル置換ピラゾロピリジンおよびその使用 |
| DE102012200357A1 (de) | 2012-01-11 | 2013-07-11 | Bayer Intellectual Property Gmbh | Fluoralkyl-substituierte Pyrazolopyridine und ihre Verwendung |
| DE102011075398A1 (de) | 2011-05-06 | 2012-11-08 | Bayer Pharma Aktiengesellschaft | Substituierte Imidazopyridazine und ihre Verwendung |
| CA2834901A1 (en) | 2011-05-06 | 2012-11-15 | Bayer Intellectual Property Gmbh | Substituted imidazopyridines and imidazopyridazines and the use thereof |
| DE102012200354A1 (de) | 2012-01-11 | 2013-07-11 | Bayer Intellectual Property Gmbh | Heteroaryl-substituierte Pyrazolopyridine und ihre Verwendung |
| CN103906752B (zh) | 2011-07-06 | 2016-08-24 | 拜耳知识产权有限责任公司 | 杂芳基取代的吡唑并吡啶及其用作可溶性鸟苷酸环化酶刺激剂的用途 |
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| WO2020164008A1 (en) | 2019-02-13 | 2020-08-20 | Bayer Aktiengesellschaft | Process for the preparation of porous microparticles |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0470039A2 (en) * | 1990-07-30 | 1992-02-05 | H. Lundbeck A/S | Novel 3-arylindole and 3-arylindazole derivatives |
| EP0667345A1 (en) * | 1994-02-14 | 1995-08-16 | Yung Shin Pharm. Ind. Co. Ltd. | 1-Benzyl-3-(substituted aryl)-condensed pyrazole derivatives as inhibitors of platelet aggregation |
-
1996
- 1996-10-14 DE DE19642255A patent/DE19642255A1/de not_active Withdrawn
-
1997
- 1997-10-01 NZ NZ335091A patent/NZ335091A/xx unknown
- 1997-10-01 HU HU9903885A patent/HUP9903885A3/hu unknown
- 1997-10-01 WO PCT/EP1997/005381 patent/WO1998016223A1/de not_active Ceased
- 1997-10-01 AT AT97913132T patent/ATE311184T1/de not_active IP Right Cessation
- 1997-10-01 CZ CZ991292A patent/CZ129299A3/cs unknown
- 1997-10-01 US US09/284,032 patent/US6180656B1/en not_active Expired - Fee Related
- 1997-10-01 ID IDW990187D patent/ID22162A/id unknown
- 1997-10-01 ES ES97913132T patent/ES2252777T3/es not_active Expired - Lifetime
- 1997-10-01 CA CA002268314A patent/CA2268314C/en not_active Expired - Fee Related
- 1997-10-01 IL IL12931897A patent/IL129318A/en not_active IP Right Cessation
- 1997-10-01 BR BR9712304-8A patent/BR9712304A/pt not_active Application Discontinuation
- 1997-10-01 SK SK465-99A patent/SK46599A3/sk unknown
- 1997-10-01 TR TR1999/00782T patent/TR199900782T2/xx unknown
- 1997-10-01 DE DE59712501T patent/DE59712501D1/de not_active Expired - Lifetime
- 1997-10-01 JP JP10517966A patent/JP2001502318A/ja active Pending
- 1997-10-01 EE EEP199900156A patent/EE9900156A/xx unknown
- 1997-10-01 EP EP97913132A patent/EP0932403B1/de not_active Expired - Lifetime
- 1997-10-01 AU AU50494/98A patent/AU733967B2/en not_active Ceased
- 1997-10-01 PL PL97332719A patent/PL332719A1/xx unknown
- 1997-10-14 TW TW086115207A patent/TW442482B/zh not_active IP Right Cessation
-
1999
- 1999-04-09 NO NO991685A patent/NO991685L/no not_active Application Discontinuation
-
2009
- 2009-02-25 JP JP2009042383A patent/JP2009114205A/ja active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0470039A2 (en) * | 1990-07-30 | 1992-02-05 | H. Lundbeck A/S | Novel 3-arylindole and 3-arylindazole derivatives |
| EP0667345A1 (en) * | 1994-02-14 | 1995-08-16 | Yung Shin Pharm. Ind. Co. Ltd. | 1-Benzyl-3-(substituted aryl)-condensed pyrazole derivatives as inhibitors of platelet aggregation |
Non-Patent Citations (1)
| Title |
|---|
| BLOOD, VOL.87, NO.9, 1 MAY 1996, PAGES 3758-3767 * |
Also Published As
| Publication number | Publication date |
|---|---|
| TW442482B (en) | 2001-06-23 |
| BR9712304A (pt) | 1999-08-31 |
| CA2268314C (en) | 2006-12-12 |
| EP0932403B1 (de) | 2005-11-30 |
| ATE311184T1 (de) | 2005-12-15 |
| HUP9903885A3 (en) | 2000-12-28 |
| AU5049498A (en) | 1998-05-11 |
| CZ129299A3 (cs) | 1999-07-14 |
| US6180656B1 (en) | 2001-01-30 |
| WO1998016223A1 (de) | 1998-04-23 |
| NO991685D0 (no) | 1999-04-09 |
| IL129318A0 (en) | 2000-02-17 |
| NO991685L (no) | 1999-04-09 |
| SK46599A3 (en) | 2000-02-14 |
| DE19642255A1 (de) | 1998-04-16 |
| ID22162A (id) | 1999-09-09 |
| TR199900782T2 (xx) | 1999-07-21 |
| EP0932403A1 (de) | 1999-08-04 |
| IL129318A (en) | 2001-06-14 |
| EE9900156A (et) | 1999-12-15 |
| CA2268314A1 (en) | 1998-04-23 |
| HUP9903885A2 (hu) | 2000-11-28 |
| ES2252777T3 (es) | 2006-05-16 |
| JP2001502318A (ja) | 2001-02-20 |
| DE59712501D1 (de) | 2006-01-05 |
| JP2009114205A (ja) | 2009-05-28 |
| PL332719A1 (en) | 1999-10-11 |
| NZ335091A (en) | 2000-09-29 |
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