- Preparation method and intermediate of chiral diamine compound
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The present invention relates to a preparation method and an intermediate of a chiral diamine compound, wherein the chiral diamine compound is used for preparing the key intermediate of a small molecule oral anticoagulant edoxaban. According to the present invention, the steps of the preparation method of the chiral diamine compound 2 and the key intermediate 2B are defined in the specification, wherein the group R is preferably selected from methoxy, ethoxy and dimethylamino.
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Paragraph 0040; 0041; 0042
(2019/07/04)
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- An efficient stereoselective synthesis of six stereoisomers of 3, 4-diaminocyclohexane carboxamide as key intermediates for the synthesis of factor Xa inhibitors
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An efficient stereoselective route for the preparation of six stereoisomers of tert-butyl ((1R, 2S, 5S)-2-amino-5-(dimethylcarbamoyl)cyclohexyl)carbamate 1 starting from simple 3-cyclohexene-1-carboxylic acid has been described. Stereochemistry of the tit
- Wang, Xin,Ma, Mingliang,Reddy, Alavala Gopi Krishna,Hu, Wenhao
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p. 1381 - 1388
(2017/02/18)
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- Discovery of N-[(1R,2S,5S)-2-{[(5-chloroindol-2-yl)carbonyl]amino}-5-(dimethylcarbamoyl)cyclohexyl]-5-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine-2-carboxamide hydrochloride: A novel, potent and orally active direct inhibitor of factor Xa
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In the early 1990's, we reported on the low-molecular selective fXa inhibitor DX-9065a having two amidino groups. However, it had poor oral bioavailability due to its strong basic amidino groups. To obtain fXa inhibitors with improved oral bioavailability
- Nagata, Tsutomu,Yoshino, Toshiharu,Haginoya, Noriyasu,Yoshikawa, Kenji,Nagamochi, Masatoshi,Kobayashi, Syozo,Komoriya, Satoshi,Yokomizo, Aki,Muto, Ryo,Yamaguchi, Mitsuhiro,Osanai, Ken,Suzuki, Makoto,Kanno, Hideyuki
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experimental part
p. 1193 - 1206
(2009/08/08)
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- Design, synthesis, and SAR of cis-1,2-diaminocyclohexane derivatives as potent factor Xa inhibitors. Part I: Exploration of 5-6 fused rings as alternative S1 moieties
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A series of cis-1,2-diaminocyclohexane derivatives were synthesized with the aim of optimizing previously disclosed factor Xa (fXa) inhibitors. The exploration of 5-6 fused rings as alternative S1 moieties resulted in two compounds which demonstrated improved solubility and reduced food effect compared to the clinical candidate, compound A. Herein, we describe the synthesis and structure-activity relationship (SAR), together with the physicochemical properties and pharmacokinetic (PK) profiles of some prospective compounds.
- Yoshikawa, Kenji,Yokomizo, Aki,Naito, Hiroyuki,Haginoya, Noriyasu,Kobayashi, Shozo,Yoshino, Toshiharu,Nagata, Tsutomu,Mochizuki, Akiyoshi,Osanai, Ken,Watanabe, Kengo,Kanno, Hideyuki,Ohta, Toshiharu
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experimental part
p. 8206 - 8220
(2010/04/06)
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- OPTICALLY ACTIVE DIAMINE DERIVATIVE AND PROCESS FOR PRODUCING THE SAME
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The invention is directed to a process for producing intermediates of a compound which exhibits an activated blood coagulation factor Xa inhibitory action and which is a useful preventive and a therapeutic agent for thrombotic diseases. The intermediate production process is represented by the following reaction scheme.
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Page/Page column 46
(2008/12/05)
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- Diamine derivatives
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A compound represented by the general formula (1): Q1-Q2-T0-N(R1)-Q3-N(R2)-T1-Q4??(1) wherein R1 and R2 are hydrogen atoms or the like; Q1 is a saturated or unsaturated, 5- or 6-membered cyclic hydrocarbon group which may be substituted, or the like; Q2 is a single bond or the like; Q3 is a group in which Q5 is an alkylene group having 1 to 8 carbon atoms, or the like; and T0 and T1 are carbonyl groups or the like; a salt thereof, a solvate thereof, or an N-oxide thereof. The compound is useful as an agent for preventing and/or treating cerebral infarction, cerebral embolism, myocardial infarction, angina pectoris, pulmonary infarction, pulmonary embolism, Buerger's disease, deep venous thrombosis, disseminated intravascular coagulation syndrome, thrombus formation after valve or joint replacement, thrombus formation and reocclusion after angioplasty, systemic inflammatory response syndrome (SIRS), multiple organ dysfunction syndrome (MODS), thrombus formation during extracorporeal circulation, or blood clotting upon blood drawing.
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- DIAMINE DERIVATIVES
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A compound represented by the general formula (1):Q1-Q2-T0-N(R1)-Q3-N(R2)-T1-Q4 wherein R1 and R2 are hydrogen atoms or the like; Q1 is a saturated or unsaturated, 5- or 6- membered cyclic hydrocarbon group which may be substituted, or the like; Q2 is a single bond or the like; Q3 is a group in which Q5 is an alkylene group having 1 to 8 carbon atoms, or the like; and T0 and T1 are carbonyl groups or the like; a salt thereof, a solvate thereof, or an N-oxide thereof. The compound is useful as an agent for preventing and/or treating cerebral infarction, cerebral embolism, myocardial infarction, angina pectoris, pulmonary infarction, pulmonary embolism, Buerger's disease, deep venous thrombosis, disseminated intravascular coagulation syndrome, thrombus formation after valve or joint replacement, thrombus formation and reocclusion after angioplasty, systemic inflammatory response syndrome (SIRS), multiple organ dysfunction syndrome (MODS), thrombus formation during extracorporeal circulation, or blood clotting upon blood drawing.
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- ETHYLENEDIAMINE DERIVATIVES
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The invention relates a compound represented by the formula (1):Q1-Q2-C(=O)-N(R1)-Q3-N(R2)-T1-Q4 wherein R1 and R2 represent H or the like; Q1 represents an aromatic ring, heterocyclic ring or the like; Q2 represents a single bond, aromatic ring, heterocyclic ring or the like; Q3 represents a group or the like, Q4 represents an aromatic ring, heterocyclic ring or the like; and T1 represents -CO- or -SO2-, and a medicine which comprises the compound and is useful for thrombosis and embolism.
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