CL2004000376A1 - Compuestos derivados de fenil propil amidas n-(aminoiminometil o aminometil) susttiuidas; compuestos intermediarios; composicion farmaceutica; y su uso para tratar un efecto patologico de la trombina, como trastornos tromboticos venosos o arteriales. - Google Patents

Compuestos derivados de fenil propil amidas n-(aminoiminometil o aminometil) susttiuidas; compuestos intermediarios; composicion farmaceutica; y su uso para tratar un efecto patologico de la trombina, como trastornos tromboticos venosos o arteriales.

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Publication number
CL2004000376A1
CL2004000376A1 CL200400376A CL2004000376A CL2004000376A1 CL 2004000376 A1 CL2004000376 A1 CL 2004000376A1 CL 200400376 A CL200400376 A CL 200400376A CL 2004000376 A CL2004000376 A CL 2004000376A CL 2004000376 A1 CL2004000376 A1 CL 2004000376A1
Authority
CL
Chile
Prior art keywords
compounds
aminoiminometil
substanced
aminometil
thrombine
Prior art date
Application number
CL200400376A
Other languages
English (en)
Inventor
Kevin R. Guertin
Scott I. Klein
Alfred P. Spada
Original Assignee
Aventis Pharma Inc
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Publication date
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Application filed by Aventis Pharma Inc filed Critical Aventis Pharma Inc
Publication of CL2004000376A1 publication Critical patent/CL2004000376A1/es

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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D207/325—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
    • C07D207/327—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • 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
    • 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
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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    • C07C205/57—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
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    • C07C255/58—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the carbon skeleton
    • C07C255/60—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the carbon skeleton at least one of the singly-bound nitrogen atoms being acylated
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    • C07C257/00—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines
    • C07C257/10—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. amidines
    • C07C257/18—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. amidines having carbon atoms of amidino groups bound to carbon atoms of six-membered aromatic rings
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    • C07C259/12—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. N-hydroxyamidines
    • C07C259/18—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. N-hydroxyamidines having carbon atoms of hydroxamidine groups bound to carbon atoms of six-membered aromatic rings
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    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/63—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by introduction of halogen; by substitution of halogen atoms by other halogen atoms
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    • C07D205/06—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D205/08—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams
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    • 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
    • C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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    • 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
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    • 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
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    • 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
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    • 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
    • C07D213/60—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 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
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    • 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
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    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
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    • 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
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    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
    • C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
    • C07D317/60—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D319/10—1,4-Dioxanes; Hydrogenated 1,4-dioxanes
    • C07D319/14—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems
    • C07D319/16—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C07D319/18—Ethylenedioxybenzenes, not substituted on the hetero ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • 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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  • Chemical & Material Sciences (AREA)
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  • Animal Behavior & Ethology (AREA)
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  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
  • Pyridine Compounds (AREA)
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CL200400376A 1996-01-02 2004-02-26 Compuestos derivados de fenil propil amidas n-(aminoiminometil o aminometil) susttiuidas; compuestos intermediarios; composicion farmaceutica; y su uso para tratar un efecto patologico de la trombina, como trastornos tromboticos venosos o arteriales. CL2004000376A1 (es)

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CA2241904C (en) * 1996-01-02 2004-12-21 Rhone-Poulenc Rorer Pharmaceuticals Inc. Substituted n-[(aminoiminomethyl or aminomethyl)phenyl]propyl amides
TW542822B (en) * 1997-01-17 2003-07-21 Ajinomoto Kk Benzamidine derivatives
AU8749598A (en) * 1997-08-26 1999-03-16 Ihara Chemical Industry Co. Ltd. Biarylalkylenecarbamic acid derivatives and bacteriocides for agricultural an d horticultural use
US6740682B2 (en) 1997-08-29 2004-05-25 Tularik Limited Meta-benzamidine derivatives as serine protease inhibitors
ES2224620T3 (es) * 1998-03-23 2005-03-01 Aventis Pharmaceuticals Inc. Derivados de piperidinilo y n-aminopiperidinilo.
AU758567B2 (en) * 1998-06-08 2003-03-27 Ajinomoto Co., Inc. Benzamidine derivative
CA2348740A1 (en) 1998-12-23 2000-07-06 Ruth R. Wexler Thrombin or factor xa inhibitors
CA2358091A1 (en) * 1998-12-23 2000-07-06 Eli Lilly And Company Antithrombotic amides
CZ20012350A3 (cs) 1998-12-24 2001-09-12 Aventis Pharmaceuticals Products Inc. Substituované (aminoiminomethyl nebo aminomethyl) benzoheteroarylové sloučeniny
CA2358581C (en) 1999-01-02 2010-02-02 Aventis Pharma Deutschland Gmbh Arylalkanoyl derivatives, processes for their preparation, their use and pharmaceutical compositions containing them
EP1022268A1 (en) * 1999-01-02 2000-07-26 Aventis Pharma Deutschland GmbH Arylalkanoyl derivatives, processes for their preparation, their use and pharmaceutical compositions containing them
US6794412B1 (en) * 1999-03-11 2004-09-21 Bristol-Myers Squibb Pharma Company Treatment of thrombosis by combined use of a factor Xa inhibitor and aspirin
US6855715B1 (en) 1999-06-14 2005-02-15 Eli Lilly And Company Serine protease inhibitors
DE60027204T2 (de) * 1999-10-28 2006-11-23 Sankyo Co., Ltd. Benzamidinderivate
IL149398A0 (en) 1999-11-02 2002-11-10 Aventis Pharma Gmbh USE OF RUSSELL'S VIPER VENOM-INDUCED PLASMA FACTOR Xa ACTIVITY TO MONITOR THE ACTIVITY OF FACTOR Xa INHIBITORS
DE10006601A1 (de) 2000-02-15 2001-08-16 Clariant Gmbh Verfahren zur Herstellung von 4-(4'-Carboxyphenyl)pyridin
GB0108903D0 (en) * 2000-10-05 2001-05-30 Aventis Pharm Prod Inc Novel crystalline forms of a factor Xa inhibitor
EP1569912B1 (en) 2002-12-03 2015-04-29 Pharmacyclics, Inc. 2-(2-hydroxybiphenyl-3-yl)-1h-benzoimidazole-5-carboxamidine derivatives as factor viia inhibitors
DE102006048300A1 (de) 2006-01-26 2007-08-02 Hellstern, Peter, Prof. Dr.med. Inhibitoren des Blutgerinnungsfaktors Xa zur Verwendung als Antikoagulans
CN102438981B (zh) * 2009-04-17 2015-04-22 德国麦氏大药厂 1-氨基-1,3,3,5,5-五甲基环己烷甲磺酸盐的合成
JP2013500298A (ja) 2009-07-29 2013-01-07 サノフイ 高齢かつ腎障害の非ｓｔ上昇型心筋梗塞患者の処置のためのオタミキサバン
GB0919194D0 (en) 2009-11-02 2009-12-16 Lytix Biopharma As Compounds
BR112013024801A2 (pt) 2011-03-29 2016-12-20 Sanofi Sa formulações de otamixaban com estabilidade aprimorada
MX2013011266A (es) 2011-03-29 2014-03-27 Sanofi Sa Sal de acido benzoico de otamixaban.
US9120776B2 (en) 2011-09-22 2015-09-01 Takeda Pharmaceutical Company Limited Condensed heterocyclic compound
EP2890381A1 (en) 2012-08-31 2015-07-08 Sanofi Otamixaban for use in the treatment of non-st elevation acute coronary syndrome in patients planned to undergo coronary artery bypass grafting
DE102014108210A1 (de) 2014-06-11 2015-12-17 Dietrich Gulba Rodentizid
US10351750B2 (en) 2017-02-03 2019-07-16 Saudi Arabian Oil Company Drilling fluid compositions with enhanced rheology and methods of using same
EP4070658A1 (de) 2021-04-06 2022-10-12 BIORoxx GmbH Verwendung von blutgerinnungshemmenden verbindungen als rodentizide

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CA2241904C (en) * 1996-01-02 2004-12-21 Rhone-Poulenc Rorer Pharmaceuticals Inc. Substituted n-[(aminoiminomethyl or aminomethyl)phenyl]propyl amides

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BR9612423A (pt) 1999-12-28
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EP0906094A4 (en) 2000-05-17
DE69628856D1 (de) 2003-07-31
PT906094E (pt) 2003-11-28
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KR100348338B1 (ko) 2003-06-02
NO310719B1 (no) 2001-08-20
ATE243512T1 (de) 2003-07-15
HUP9900930A2 (hu) 1999-08-30
SI0906094T1 (en) 2003-12-31
AU1520797A (en) 1997-07-28
ES2197257T3 (es) 2004-01-01
CZ9802010A3 (cs) 1999-09-15
HUP9900930A3 (en) 2001-11-28
EP0906094B1 (en) 2003-06-25
PL327633A1 (en) 1998-12-21
NO983039D0 (no) 1998-06-30
NO983039L (no) 1998-09-02
CZ297544B6 (cs) 2007-02-07
AP861A (en) 2000-08-01
IL125163A0 (en) 1999-01-26
EP0906094A1 (en) 1999-04-07
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BR9612423B1 (pt) 2010-11-30
EA001932B1 (ru) 2001-10-22
US6140504A (en) 2000-10-31
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HU228355B1 (en) 2013-03-28
SK284507B6 (sk) 2005-05-05
CA2241904A1 (en) 1997-07-10
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JP4053597B2 (ja) 2008-02-27
AU723338B2 (en) 2000-08-24
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