- Synthesis and evaluation of novel ligands for the histamine H4 receptor based on a pyrrolo[2,3-d]pyrimidine scaffold
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Starting from a known H4R ligand based on a pyrimidine skeleton, a series of novel analogues based on a pyrrolo[2,3-d]pyrimidine scaffold have been prepared. Whereas the original pyrimidine congener shows good affinity at hH4R (Ki = 0.5 μM), its lacks selectivity with a K i value for the hH3R of 1 μM. Within the newly synthesized pyrrolo[2,3-d]pyrimidines, several congeners show Ki values of less than 1 μM at the hH4R and show a much improved selectivity profile. Therefore, these series represent an interesting starting point for the discovery of novel hH4R ligands.
- Gao, Ling-Jie,Schwed, J. Stephan,Weizel, Lilia,De Jonghe, Steven,Stark, Holger,Herdewijn, Piet
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p. 132 - 137
(2013/02/23)
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- STEREOSELECTIVE SYNTHESIS OF PIPERIDINE DERIVATIVES
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This invention relates to dialdehyde or dinitrile compounds, which are useful for stereoselective synthesis of piperidine, pyrrolidine, and azepane derivatives.
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Page/Page column 15
(2010/06/22)
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- Chiral 3-aminopyrrolidines as a rigid diamino scaffold for organocatalysis and organometallic chemistry
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Over 20 new and easily prepared diamines were screened for the asymmetric Morita-Baylis-Hillman reaction. Chiral non-racemic 3-(N,N-dimethylamino)-1- methylpyrrolidine was found to promote efficiently the reaction of methyl vinyl ketone and substituted benzaldehydes. Enantiomeric excesses up to 73% were reached with electron-deficient benzaldehyde derivatives. After a simple deprotonation, one of these diamines was transformed into a chiral mixed aggregate for the enantioselective synthesis of (R)-1-o-tolylethanol with 76% ee.
- Pouliquen, Mickael,Blanchet, Jerome,Paolis, Michael De,Rema Devi,Rouden, Jacques,Lasne, Marie-Claire,Maddaluno, Jacques
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experimental part
p. 1511 - 1521
(2010/11/02)
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- PROCESS FOR PRODUCING NITROGENOUS HETEROCYCLIC COMPOUND
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A nitrogenous heterocyclic compound such as 3-aminopyrrolidine derivative is produced by hydrogenolysis of an N-substituted nitrogenous heterocyclic compound with normal pressure hydrogen in a water-based solvent in presence of a catalyst. In the case an optically active 1-substituted-3-aminopyrrrolidine derivative is used as a raw material, an optically active 3-aminopyrrolidine derivative can be obtained as a product practically without racemination.
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Page/Page column 10-11
(2010/11/08)
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- Methods of treating insulin resistance syndrome and diabetes
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This invention is directed to methods of treating insulin resistance syndrome and diabetes in a patient in need thereof, comprising administering to said patient a pharmaceutically effective amount of a compound derived from adenosine and analogues thereof, or a pharmaceutically acceptable salt thereof, a pharmaceutically acceptable prodrug thereof, an N-oxide thereof, a hydrate thereof or a solvate thereof, or a pharmaceutical composition comprising such compound.
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- Compounds having antihypertensive, cardioprotective, anti-ischemic and antilipolytic properties
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A compound of the formula wherein K is N; Q is CH2or O; R6is hydrogen, alkyl, allyl, 2-methylallyl, 2-butenyl, or cycloalkyl where the nitrogen of the ring of X is substituted by Y; E is O or S; Y is hydrogen, alkyl, aralkyl, substituted aralkyl, aryl, substituted aryl, heterocyclyl, substituted heterocyclyl, heterocyclylalkyl, or substituted heterocyclylalkyl; and n and p are independently 0, 1, 2, or 3, provided that n+p is at least 1; T is hydrogen, alkyl, alkylcarbonyl, alkylthiocarbonyl, halo, carboxyl, A and B are independently hydrogen, alkyl, hydroxyalkyl, alkoxyalkyl, or OR′; or a pharmaceutically acceptable salt thereof, a pharmaceutic-ally acceptable prodrug thereof, an N-oxide thereof, a hydrate thereof or a solvate thereof.
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- An efficient conversion of chiral α-amino acids to enantiomerically pure 3-amino cyclic amines
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Enantiomerically pure 3-amino cyclic amines such as 3-amino pyrrolidine, 3-amino piperidine, and 2,3,4,5,6,7-hexahydro-1H-azepine have been synthesized in high yields from the optically active natural α-amino acids such as L-aspartic acid, L-glutamic acid, L-2-aminoadipic acid, and their enantiomers.
- Moon, Sung-Hwan,Lee, Sujin
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p. 3919 - 3926
(2007/10/03)
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- Practical synthesis of (S)-3-(p-nitrobenzyloxy-carbonylamino)pyrrolidine and its related compounds from L-aspartic acid
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An efficient method for the preparation of (S)-3-aminopyrrolidine derivatives was developed starting from L-aspartic acid, which involves an efficient formation of a pyrrolidine-ring from allylamine and a practical Pd/C-catalyzed cleavage of N-allyl prote
- Tomori, Hiroshi,Shibutani, Kuniko,Ogura, Katsuyuki
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p. 213 - 225
(2007/10/03)
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- Quinobenzoxazine, antineoplastic agents
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Quinobenzoxazine, derivatives of the formula STR1 as well as the pharmaceutically acceptable salts, esters, amides and prodrugs thereof are disclosed, wherein R1 is hydrogen or a carboxy-protecting group, R2 and R3 are substitutents, A is oxygen, Z is a halogen or a nitrogen-containing group, X is hydrogen, halogen or alkyl, and W is hydrogen, alkyl, amino or halogen. The compounds have potent antineoplastic activity.
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- Quinolone antibacterial agents. Synthesis and structure-activity relationships of a series of amino acid prodrugs of racemic and chiral 7-(3- amino-1-pyrrolidinyl)quinolones. Highly soluble quinolone prodrugs with in vivo pseudomonas activity
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A series of amino acid prodrugs of racemic and chiral 7-(3-amino-1- pyrrolidinyl)-6-fluoro-1,8-naphthyridine-3-carboxylic acids, 1-cyclopropyl- 6,8-difluoro-3-quinolinecarboxylic acids, 1-cyclopropyl-6-fluoro-3- quinolinecarboxylic acids, and 5-amino-1-cyclopropyl-6,8-difluoro-3- quinolinecarboxylic acids have been prepared and evaluated for comparative antibacterial activity. Compounds were prepared by acylation of the 3-amino group of the pyrrolidine with common amino acids using standard peptide chemistry. This series has been compared with the parent compounds for antibacterial activity in vitro and in vivo as well as for comparative solubility. The amino acid analogues were less active in vitro, but had equal or increased efficacy in vivo. Indeed, it was proven that these compounds, which were stable to acid and base under the reaction conditions for their preparation, were rapidly cleaved in serum to give the parent quinolones. The amino acid derivatives showed a 3-70 times improved solubility when compared to the parent compounds. The most active compound of the series was [S- (R*,R*)]-7-[3-[(2-amino-1-oxopropyl)-amino]-1-pyrrolidinyl]-1-cyclopropyl- 6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid (PD 131112).
- Sanchez,Domagala,Heifetz,Priebe,Sesnie,Trehan
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p. 1764 - 1773
(2007/10/02)
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- (S)-7-(3-amino-1-pyrrolidinyl)-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid
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The novel (S)-7-(3-amino-1-pyrrolidinyl)-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-n phthyridine-3-carboxylic acid, lower alkyl esters and pharmaceutically acceptable salts thereof are described as well as a method for its manufacture, formulation, and use in treating bacterial infections.
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- Naphthyridine antibacterial agents containing an α-amino acid in the side chain of the 7-substituent
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Novel quinolone and naphthyridine antibacterial agents are herein described having improved in vivo activity both orally and subcutaneously where the 7-side chain of such compounds contain an α-amino acid; also described are its corresponding optical isomers, methods of preparation as well as compositions and methods of treating infections diseases.
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