- Synthesis method of chiral 3-aminopiperidine and derivatives of 3-aminopiperidine
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The invention relates to a synthesis method of chiral 3-aminopiperidine and derivatives of 3-aminopiperidine. According to the synthesis method, R (or S)-piperidine-3-ethyl formate-L (or D)-tartrate is subjected to a hydrazinolysis reaction after being subjected to benzyl protection, and R or S-1-benzyl-3-aminopiperidine is obtained through azidation and Curtius rearrangement. R or S-1-benzyl-3-aminopiperidine is subjected to debenzylation, R or S-3-aminopiperidine can be obtained, R or S-1-benzyl-3-aminopiperidine is subjected to 3-t-butyloxycarboryl protection and debenzylation in sequence,R or S-(3-t-butyloxycarborylamino) piperidine can be obtained, and corresponding salts of R or S-3-aminopiperidine can be obtained through hydrolyzing deprotection of R or S-(3-t-butyloxycarborylamino) piperidine under the acidic condition. The synthesis method of chiral 3-aminopiperidine and the derivatives of 3-aminopiperidine is low in cost, facilitates industrialization and has high optical purity.
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Paragraph 0124-0125
(2019/09/17)
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- Synthetic method for (R)-N-tert-butoxycarbonyl-3-hydroxymethylpiperidine
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The invention discloses a synthetic method for (R)-N-tert-butoxycarbonyl-3-hydroxymethylpiperidine. The method comprises the following four steps: synthesizing ethyl 3-piperidinecarboxylate (compoundII), synthesizing ethyl (R)-nipecotate-L-tartarate (compound III), synthesizing ethyl (R)-N-Boc-3-piperidinecarboxylate (compound IV) and synthesizing the (R)-N-tert-butoxycarbonyl-3-hydroxymethylpiperidine (compound V); and the method comprises the following special steps: synthesizing the compound II by using 3-piperidinecarboxylic acid (compound I) as a raw material through chloroacylation andethanol esterification; performing a salt formation reaction to form the compound III; adding a Boc anhydride and performing a reaction to obtain the compound IV; and finally performing sodium borohydride reduction to obtain the compound V. The method provided by the invention has the advantages of mild reaction conditions, environmental friendliness, simple operation steps, better reproducibilityand high practicability, and is suitable for industrial mass production of the (R)-N-tert-butoxycarbonyl-3-hydroxymethylpiperidine.
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- FARNESYL PROTEIN TRANSFERASE INHIBITORS
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Disclosed are compounds of formula (1.0), wherein R represents a cyclic moiety to which is bound an imodazolylalkyl group; R represents a carbamate, urea, amide or sulfonamide group; and the remaining substituents are as defined herein. Also disclosed is a method of treating cancer and a method of inhibiting farnesyl protein transferase using the disclosed compounds.
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Page/Page column 33
(2010/02/11)
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- Novel farnesyl protein transferase inhibitors as antitumor agents
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Disclosed are novel tricyclic compounds represented by the formula (1.0): and a pharmaceutically acceptable salt or solvate thereof. The compounds are useful for inhibiting farnesyl protein transferase. Also disclosed are pharmaceutical compositions comprising compounds of formula 1.0. Also disclosed are methods of treating cancer using the compounds of formula 1.0.
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- A Practical Synthesis of the Platelet Fibrinogen Antagonist, Elarofiban
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Elarofiban is a novel, nonpeptide, orally active fibrinogen receptor antagonist useful for the treatment of platelet mediated thrombotic disorders (Costanzo, M. J.; Hoekstra, W. J.; Maryanoff, B. E. WO, 97/41102,1997). Herein we describe the process research that was carried out for the synthesis of elarofiban that eventually led to the development of a safe and cost-effective commercial scale process.
- Cohen, Judith H.,Roessler, Armin,Scott, Lorraine,Sorgi, Kirk L.,Villani Jr., Frank J.,Webster, Robin R. H.,Weh, Christian,Bos, Mary Ellen,Cesco-Cancian, Sergio,Harris, Bruce D.,Hortenstine, John T.,Justus, Michael,Maryanoff, Cynthia A.,Mills, John,Muller, Stefan
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p. 866 - 872
(2013/09/05)
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- N-[(R)-1-[3-(4-piperidyl)propionyl]-3-piperidylcarbonyl]-2(S)-acetylamino-β-alanine trihydrate, compositions thereof, and methods for its use
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The trihydrates of β-alanine of the formula Are disclosed. Also method of antogonizing glycoprotein IIb/IIIa activity using these compounds is also disclosed.
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- Novel farnesyl protein transferase inhibitors as antitumor agents
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Disclosed are novel tricyclic compounds represented by the formula (1.0): or a pharmaceutically acceptable salt or solvate thereof. The compounds are useful for inhibiting farnesyl protein transferase. Also disclosed are pharmaceutical compositions comprising compounds of formula 1.0. Also disclosed are methods of treating cancer using the compounds of formula 1.0.
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- Beta lactam compounds and their use as inhibitors of tryptase
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Compounds of the formulas: are disclosed. These compounds inhibit tryptase as well as other enzyme systems or are selective tryptase inhibitors and are useful as antiinflammatory agents particularly in the treatment of chronic asthma.
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Page column 253
(2010/11/29)
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- Phenoxymethyl piperidine derivatives for the treatment of neuropathic pain
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Compounds selected from the group of compounds represented by Formula I: as an individual isomer or as a racemic or non-racemic mixture of isomers, and their pharmaceutically acceptable salts and N-oxides thereof; are sodium channel blockers, and thus exh
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- Oligomers of β2- and of β3-homoproline: What are the secondary structures of β-peptides lacking H-bonds?
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To study the role of H-bonds in stabilizing β-peptidic secondary structures, we have synthesized β-oligopeptides (up to the octadecamer 12) consisting of β2- and β3-homoproline, i.e., β-peptides lacking amide protons. The enantiomer purity of the building block β2-homoproline (nipecotic acid, 4) was determined by HPLC analysis of the N-(2,4- dinitrophenyl) derivative 5 on a Chiralcel-OD column (cf. Fig. 2). The CD spectra of the all-(S)-β2- and all-(S)-β3-HPro-containing, β-peptides display novel and intensive CD patterns which may be indicative of a secondary structure (cf. Fig. 3). It is noteworthy that a distinct CD pattern was observed with the β3-HPro derivatives containing as few as three residues (7a). The crystal structure of a N-deprotected β3-HPro-tripeptide 7c is presented (cf. Figs. 4 and 5), and a model for the structure of β- peptides consisting of β3-HPro is discussed (cf. Figs. 6 and 7).
- Abele, Stefan,Voegtli, Kurt,Seebach, Dieter
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p. 1539 - 1558
(2007/10/03)
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