60080-69-5

Usage

InChI:InChI=1/C6H14N2O2.ClH/c1-10-6(9)5(8)3-2-4-7;/h5H,2-4,7-8H2,1H3;1H/t5-;/m0./s1

Upstream product

• 67-56-1 methanol 
• 3184-13-2 L-ornithine hydrochloride 
• 207734-73-4 L-ornithine monohydrate 
• 108-20-3 di-isopropyl ether 
• 16682-12-5 D-ornithine hydrochloride 

Downstream Products

• 42538-31-8 (3S)-3-aminopiperidin-2-one hydrochloride 
• 95582-17-5 (S)-3-[[(phenylmethoxy)carbonyl]amino]-2-oxopiperidine 
• 307345-39-7 (3S)-3-benzyloxycarbonylamino-1-diaminophosphinyl-2-piperidinone 
• 308103-74-4 4-(3-amino-1-methoxypropyl)-1,3-dihydro-2-imidazolone 
• 875924-43-9 C₂₀H₁₈Cl₄N₂O₂ 
• 875924-44-0 C₂₀H₁₈Cl₄N₂O₂ 
• 69955-51-7 methyl (S)-2,5-bis((benzylidene)amino)pentanoate 
• 875924-42-8 C₂₀H₂₀Cl₂N₂O₂ 
• 875924-45-1 C₂₀H₂₀N₄O₆ 

Relevant academic research and scientific papers

Novel chiral derivatizing agents for 1H NMR determination of enantiomeric purities of carboxylic acids

(S)-4-(3-Aminopyrrolidin-1-yl)coumarin (1), (S)-4-(3-aminopiperidin-1-yl)coumarin (4), and (S)-4-(3-aminoazepan-1-yl)coumarin (7), prepared from 4-chlorocoumarin and (S)-pyrrolidin-3-amine, (S)-piperidin-3-amine, and (S)-azepan-3-amine, respectively, were proven to be versatile and reliable 1H NMR optical purity determination agents for chiral carboxylic acids.

ANTI-INFLAMMATORY COMPOSITION

The invention relates to 3-(2',2'-dimethylpropanoylamino)-tetrahydropyridin-2-one, and its pharmaceutical compositions and its use for preparing a medicament intended to prevent or treat inflammatory disorders.

Development of a large-scale synthesis of sulphostin, a dipeptidyl peptidase IV inhibitor

For the progress of the in vivo study on sulphostin, a dipeptidyl peptidase IV inhibitor, its large-scale synthetic method was investigated. The optical resolution of (3S,RSP)-1-amino(sulfoamino)phosphinyl-3- benzyloxycarbonylamino-2-piperidinone, which was the most difficult step in the previous method, was simplified by using fractional crystallization. The use of 2 mol equiv of (1S,2R)-(+)-2-amino-1,2-diphenylethanol for optical resolution gave desired diastereomer 15 in good yield as a less soluble salt. In the present synthetic method, there were no requirements for purification using column chromatography, reaction at cryogenic temperature, and treatment using the haloalkane solvents. The total yield of the new method was 4.6%, which was an improvement of approximately 2-fold compared to the method reported previously.

First synthesis and determination of the absolute configuration of sulphostin, a novel inhibitor of dipeptidyl peptidase IV

Sulphostin, a novel dipeptidyl peptidase IV (DPP-IV) inhibitor, was isolated from the culture broth of Streptomyces sp. MK251-43F3. Determination of the absolute configurations of two asymmetric atoms using the natural product was not achieved due to the small amount of the compound obtained. We synthesized four possible stereoisomers of sulphostin from D- or L-ornithine and compared their physicochemical and biological data to naturally isolated sulphostin. As a result, the absolute configurations at C-3 and the phosphorus atom of sulphostin were determined to be S and R, respectively, by X-ray crystallography. Synthetic sulphostin and its C-3 epimer have strong inhibitory activities against DPP-IV, IC50 values of which are 6.0 and 8.9 ng/mL, respectively. Thus it appears that the configuration of the phosphorus atom is primarily responsible for the activity; in contrast, the configuration of C-3 does not appear to affect the activity.

NEW HETEROCYCLIC AMIDE COMPOUNDS USEFUL FOR THE TREATMENT OF INFLAMMATORY AND ALLERGIC DISORDERS: PROCESS FOR THEIR PREPARATION AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM

The present invention relates to novel heterocyclic compounds that inhibit phosphodiesterase type 4 (PDE 4). The compounds are useful for treating inflammatory conditions, diseases of the central nervous systems and insulin resistant diabetes.

Sulphostin analogue and process for producing sulphostin and its analogue

A sulphostin analogue represented by the general formula, wherein n is an integer of from 0 to 3, provided that a case where n is 2 and steric configurations of C* and P* are S and R, respectively, is excluded, or a pharmaceutically acceptable salt thereof.

Design, synthesis, and preliminary pharmacological evaluation of N-Acyl-3-aminoglutarimides as broad-spectrum chemokine inhibitors in vitro and anti-inflammatory agents in vivo

A series of N-substituted 3-aminoglutarimides have been synthesized and tested for inhibitory activity against a range of chemokines in vitro and for suppression of lipopolysaccharide-induced inflammation in vivo. The results show that they represent the first class of small molecules with broad-spectrum chemokine inhibitory effects. Among the compounds studied, 10 (NR58,4) was the most potent, being active at doses between 5 and 15 nM in vitro and at 0.3 mg kg-1 in vivo.

A chiral sensor for arginine and lysine

(Graph presented) We provide access to a new class of C1-or C2-symmetrical host molecules 1 and 2 based on a spirobisindane skeleton. Whereas 1 is selective for short, rigid diamines, 2 prefers longer α,ω-dications. Of all the amino acid methyl esters, only those of lysine and arginine with the correct distance between their cationic groups form strong 1:1 complexes in DMSO with 2. NMR titrations reveal high association constants as well as discrimination between the enantiomers of lysine and arginine.

Novel quinolonecarboxylic acid derivatives

Novel compounds of the present invention are represented by the general formula (1) STR1 wherein R1 is hydrogen atom or amino, R2 is fluorine atom or methoxy, R3 is hydrogen atom or a lower alkyl having 1 to 3 carbon atoms, and n is 0 or 1. The compounds of the general formula (1) exhibit higher antibacterial activity with fewer side-effects than known quinolone antibiotics such as ofloxacin and norfloxacin. Further, the compounds having the general formula (1) have reduced phototoxicity which normally accompanies 6,8-defluoroquinoline antibiotics.

NEW CHIRAL AMINOPHOSPHINES PREPARED FROM L-ORNITHINE AND CATALYTIC ASYMMETRIC HYDROGENATION USING THEIR RHODIUM(I) COMPLEXES

From readily preparable chiral diamines were obtained new aminophosphines, (3S)--3-aminopiperidine, and (3S)--3-(methylamino)piperidine.Asymmetric hydrogenation of α-acylaminoacrylic acids, employing Rh(I) complexes with these aminophosphines as catalyst, gave optically active N-acyl-α-amino acids.