SK286856B6 - N-Guanidinoalkylamidy, spôsob ich prípravy, použitie a farmaceutické prostriedky, ktoré ich obsahujú - Google Patents

N-Guanidinoalkylamidy, spôsob ich prípravy, použitie a farmaceutické prostriedky, ktoré ich obsahujú Download PDF

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Publication number
SK286856B6
SK286856B6 SK578-2002A SK5782002A SK286856B6 SK 286856 B6 SK286856 B6 SK 286856B6 SK 5782002 A SK5782002 A SK 5782002A SK 286856 B6 SK286856 B6 SK 286856B6
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SK
Slovakia
Prior art keywords
group
formula
groups
alkyl
carbon atoms
Prior art date
Application number
SK578-2002A
Other languages
English (en)
Slovak (sk)
Other versions
SK5782002A3 (en
Inventor
Otmar Klingler
Gerhard Zoller
Elisabeth Defossa
Fahad Al-Obeidi
Armin Walser
James Ostrem
Original Assignee
Sanofi-Aventis Deutschland Gmbh
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Sanofi-Aventis Deutschland Gmbh filed Critical Sanofi-Aventis Deutschland Gmbh
Publication of SK5782002A3 publication Critical patent/SK5782002A3/sk
Publication of SK286856B6 publication Critical patent/SK286856B6/sk

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
    • C07D213/30—Oxygen atoms
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • 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
    • A61P9/10—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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
    • C07C279/04—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to acyclic carbon atoms of a carbon skeleton
    • C07C279/14—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to acyclic carbon atoms of a carbon skeleton being further substituted by carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/36—Radicals substituted by singly-bound nitrogen atoms
    • C07D213/40—Acylated substituent nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/20—Oxygen atoms
    • C07D215/22—Oxygen atoms attached in position 2 or 4
    • C07D215/233—Oxygen atoms attached in position 2 or 4 only one oxygen atom which is attached in position 4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/32—One oxygen, sulfur or nitrogen atom
    • C07D239/34—One oxygen atom

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Engineering & Computer Science (AREA)
  • Cardiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Pain & Pain Management (AREA)
  • Hematology (AREA)
  • Urology & Nephrology (AREA)
  • Vascular Medicine (AREA)
  • Diabetes (AREA)
  • Rheumatology (AREA)
  • Pulmonology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Quinoline Compounds (AREA)
  • Pyridine Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
SK578-2002A 1999-10-30 2000-10-21 N-Guanidinoalkylamidy, spôsob ich prípravy, použitie a farmaceutické prostriedky, ktoré ich obsahujú SK286856B6 (sk)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP99121623A EP1095933A1 (en) 1999-10-30 1999-10-30 Novel N-guanidinoalkylamides, their preparation, their use, and pharmaceutical preparations comprising them
PCT/EP2000/010395 WO2001032611A1 (en) 1999-10-30 2000-10-21 N-guanidinoalkylamides, their preparation, their use, and pharmaceutical preparations comprising them

Publications (2)

Publication Number Publication Date
SK5782002A3 SK5782002A3 (en) 2002-10-08
SK286856B6 true SK286856B6 (sk) 2009-06-05

Family

ID=8239305

Family Applications (1)

Application Number Title Priority Date Filing Date
SK578-2002A SK286856B6 (sk) 1999-10-30 2000-10-21 N-Guanidinoalkylamidy, spôsob ich prípravy, použitie a farmaceutické prostriedky, ktoré ich obsahujú

Country Status (31)

Country Link
US (2) US6472562B1 (enExample)
EP (2) EP1095933A1 (enExample)
JP (1) JP4658430B2 (enExample)
KR (1) KR100981593B1 (enExample)
CN (1) CN1249026C (enExample)
AR (1) AR026257A1 (enExample)
AT (1) ATE264837T1 (enExample)
AU (1) AU776797B2 (enExample)
BR (1) BR0015186A (enExample)
CA (1) CA2389412C (enExample)
CZ (1) CZ301855B6 (enExample)
DE (1) DE60010113T2 (enExample)
DK (1) DK1228039T3 (enExample)
EE (1) EE05168B1 (enExample)
ES (1) ES2220553T3 (enExample)
HR (1) HRP20020372B1 (enExample)
HU (1) HUP0203627A3 (enExample)
IL (2) IL149209A0 (enExample)
ME (1) MEP54708A (enExample)
MX (1) MXPA02003805A (enExample)
NO (1) NO328016B1 (enExample)
NZ (1) NZ518607A (enExample)
PL (1) PL203859B1 (enExample)
PT (1) PT1228039E (enExample)
RS (1) RS50471B (enExample)
RU (1) RU2253651C2 (enExample)
SI (1) SI1228039T1 (enExample)
SK (1) SK286856B6 (enExample)
TR (1) TR200201181T2 (enExample)
WO (1) WO2001032611A1 (enExample)
ZA (1) ZA200203294B (enExample)

Families Citing this family (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP4579240B2 (ja) * 2003-07-04 2010-11-10 ロンザ アーゲー 担持相合成法の改善
SI2915564T1 (sl) 2007-09-28 2021-03-31 Alexion Pharmaceuticals, Inc. Antidoti za zaviralce dejavnika Ksa in postopki njihove uporabe
US8193182B2 (en) 2008-01-04 2012-06-05 Intellikine, Inc. Substituted isoquinolin-1(2H)-ones, and methods of use thereof
KR101653842B1 (ko) 2008-01-04 2016-09-02 인텔리카인, 엘엘씨 특정 화학 물질, 조성물 및 방법
RU2377990C1 (ru) * 2008-07-23 2010-01-10 Федеральное Государственное Образовательное Учреждение Высшего Профессионального Образования "Южный Федеральный Университет" Антитромботическое средство, влияющее на регуляцию функциональной активности тромбоцитов
US8455439B2 (en) 2008-11-14 2013-06-04 Portola Pharmaceuticals, Inc. Antidotes for factor Xa inhibitors and methods of using the same in combination with blood coagulating agents
FI3604510T3 (fi) 2009-03-30 2025-06-26 Alexion Pharma Inc Vastalääkkeitä tekijä xa:n estäjille ja menetelmiä niiden käyttämiseksi
PT2453910T (pt) 2009-07-15 2016-12-07 Portola Pharm Inc Formulação de dose unitária de antídoto contra inibidores de fator xa para uso na prevenção de sangramento
AR084824A1 (es) 2011-01-10 2013-06-26 Intellikine Inc Procesos para preparar isoquinolinonas y formas solidas de isoquinolinonas
US8828998B2 (en) 2012-06-25 2014-09-09 Infinity Pharmaceuticals, Inc. Treatment of lupus, fibrotic conditions, and inflammatory myopathies and other disorders using PI3 kinase inhibitors
WO2014071109A1 (en) 2012-11-01 2014-05-08 Infinity Pharmaceuticals, Inc. Treatment of cancers using pi3 kinase isoform modulators
WO2015160975A2 (en) 2014-04-16 2015-10-22 Infinity Pharmaceuticals, Inc. Combination therapies
RU2754507C2 (ru) 2016-06-24 2021-09-02 Инфинити Фармасьютикалз, Инк. Комбинированная терапия
CN110357800B (zh) * 2018-04-09 2022-07-26 青岛海生洋润生物科技有限公司 脯氨酸衍生物及其在制备治疗心脑血管疾病药物中的应用
CN115317474A (zh) * 2021-05-10 2022-11-11 中国海洋大学 一种苯酰胍衍生物在用于制备预防和治疗神经系统疾病或心血管系统疾病的药物中的应用

Family Cites Families (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
HU206372B (en) * 1990-09-03 1992-10-28 Richter Gedeon Vegyeszet Process for producing new oligopeptides which selectively inhibit proliferation of haemopoietic cells and pharmaceutical compositions comprising same
US5506134A (en) 1990-10-22 1996-04-09 Corvas International, Inc. Hypridoma and monoclonal antibody which inhibits blood coagulation tissue factor/factor VIIa complex
US5833982A (en) 1991-02-28 1998-11-10 Zymogenetics, Inc. Modified factor VII
US5788965A (en) 1991-02-28 1998-08-04 Novo Nordisk A/S Modified factor VII
US5371072A (en) * 1992-10-16 1994-12-06 Corvas International, Inc. Asp-Pro-Arg α-keto-amide enzyme inhibitors
JPH08506225A (ja) 1993-01-20 1996-07-02 ジョン アリグザンドロビクス，ピーター ラインモニタシステム
DE4326465A1 (de) 1993-01-20 1995-02-09 Thomae Gmbh Dr K Aminosäurederivate, diese Verbindungen enthaltende Arzneimittel und Verfahren zu ihrer Herstellung
NZ263084A (en) * 1993-03-12 1997-08-22 Arris Pharm Corp Dipeptide derivatives, treatment of immunomediated inflammatory disorders
CZ296439B6 (cs) 1994-04-26 2006-03-15 Selectide Corporation Inhibitory faktoru Xa
CA2206532C (en) * 1994-12-02 2006-07-11 Yamanouchi Pharmaceutical Co., Ltd. Novel amidinonaphthyl derivative or salt thereof
US6342504B1 (en) * 1994-12-13 2002-01-29 Corvas International, Inc. Aromatic heterocyclic derivatives as enzyme inhibitors
IL134394A0 (en) * 1997-08-27 2001-04-30 Kissei Pharmaceutical 3-amidinoaniline derivatives, activated blood coagulation factor x inhibitors, and intermediates for producing both
SE9703414D0 (sv) * 1997-09-23 1997-09-23 Astra Ab New compounds
PL195682B1 (pl) 1997-12-24 2007-10-31 Sanofi Aventis Deutschland Pochodne indolu, sposób ich wytwarzania, środek farmaceutyczny oraz zastosowanie pochodnych indolu
AU2074699A (en) * 1998-01-26 1999-08-09 Yamanouchi Pharmaceutical Co., Ltd. Novel benzene-fused heterocyclic derivatives or salts thereof
EP0987274A1 (en) 1998-09-15 2000-03-22 Hoechst Marion Roussel Deutschland GmbH Factor VIIa Inhibitors
JP2002543130A (ja) * 1999-05-05 2002-12-17 メルク エンド カムパニー インコーポレーテッド 抗微生物剤としての新規なカテコール類

Also Published As

Publication number Publication date
EP1095933A1 (en) 2001-05-02
MXPA02003805A (es) 2004-10-15
PL354808A1 (en) 2004-02-23
BR0015186A (pt) 2002-07-23
YU29702A (sh) 2005-06-10
NO20022022D0 (no) 2002-04-29
AU776797B2 (en) 2004-09-23
NZ518607A (en) 2003-10-31
PT1228039E (pt) 2004-09-30
SK5782002A3 (en) 2002-10-08
RU2253651C2 (ru) 2005-06-10
ZA200203294B (en) 2003-01-29
PL203859B1 (pl) 2009-11-30
IL149209A0 (en) 2002-11-10
RS50471B (sr) 2010-03-02
EE200200199A (et) 2003-06-16
HRP20020372B1 (hr) 2011-01-31
WO2001032611A1 (en) 2001-05-10
DK1228039T3 (da) 2004-08-16
US6664393B2 (en) 2003-12-16
CA2389412A1 (en) 2001-05-10
CN1249026C (zh) 2006-04-05
AR026257A1 (es) 2003-02-05
CN1387508A (zh) 2002-12-25
TR200201181T2 (tr) 2002-09-23
JP4658430B2 (ja) 2011-03-23
US20030162967A1 (en) 2003-08-28
NO328016B1 (no) 2009-11-09
RU2002114041A (ru) 2004-01-20
AU1026501A (en) 2001-05-14
HK1050673A1 (en) 2003-07-04
IL149209A (en) 2007-06-03
CA2389412C (en) 2009-12-01
HUP0203627A3 (en) 2004-12-28
HUP0203627A2 (hu) 2003-03-28
EE05168B1 (et) 2009-06-15
DE60010113D1 (de) 2004-05-27
EP1228039A1 (en) 2002-08-07
KR100981593B1 (ko) 2010-09-13
SI1228039T1 (en) 2004-10-31
JP2003513066A (ja) 2003-04-08
CZ20021489A3 (cs) 2002-07-17
KR20020047310A (ko) 2002-06-21
MEP54708A (en) 2011-05-10
HRP20020372A2 (en) 2004-08-31
CZ301855B6 (cs) 2010-07-14
US6472562B1 (en) 2002-10-29
DE60010113T2 (de) 2005-05-04
NO20022022L (no) 2002-04-29
ATE264837T1 (de) 2004-05-15
ES2220553T3 (es) 2004-12-16
EP1228039B1 (en) 2004-04-21

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MM4A Patent lapsed due to non-payment of maintenance fees

Effective date: 20131021