149868-39-3Relevant academic research and scientific papers
Synthesis of Am80 (tamibarotene) prodrug candidates, congeners and metabolites
Muratake, Hideaki,Amano, Yohei,Toda, Takahiro,Sugiyama, Kiyoshi,Shudo
, p. 846 - 852 (2013/09/12)
Compound 1 (IT-M-07000) was previously reported as a candidate prodrug of Am80 (Tamibarotene; used to treat acute promyelocytic leukemia), and shown to be efficiently metabolized to Am80 via β-oxidation. Here, we describe in detail the synthesis of 1, together with another tetradeuterated candidate prodrug, IT-YA-00616 (2), as well as two congeners, and several metabolic intermediates of 1 previously detected in mouse plasma.
RETINOID PRODRUG COMPOUND
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Page/Page column 16, (2010/08/18)
A compound represented by the following general formula (I) : [R1 to R5 represent hydrogen atom, an alkyl group, or a trialkylsilyl group, X represents -NH-CO-, -CO-NH-, -N(COR6)-CO-, -CO-N(COR7)- (R6 and R7 represent a lower alkoxy group, or a carboxy-substituted phenyl group) etc.; and Z represents -Y-CH(R12)-COOH, -CHO, -CH-CH-COOH, or -COOR13 (Y represents a single bond, -CH2-, -CH(OH)-, -CO-, -CO-NH-, or -CO-NH-CH2-CO-NH-, R12 represents hydrogen atom or a lower alkyl group, and R13 represents hydrogen atom, -CH(R14)-COOH (R14 represents hydrogen atom, a lower alkyl group, or hydroxy group), -[CH2CH2-O]n-CH2-CH2-OH, CH2-O-[CH2CH2O]m-CH2-OH, or -[CH(CH3)-CO-O]p-CH(CH3)-COOH (m, n and p represent an integer of 1 to 100))], a salt thereof or an ester thereof, which has a property of being converted into a retinoid after absorption in vivo.
RETINOID PRODRUG COMPOUND
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Page/Page column 13, (2010/12/29)
A compound represented by the following general formula (I): [R1 to R5 represent hydrogen atom, an alkyl group, or a trialkylsilyl group, X represents —NH—CO—, —CO—NH—, —N(COR6)—CO—, —CO—N(COR7)— (R6 and R7 represent a lower alkoxy group, or a carboxy-substituted phenyl group) etc.; and Z represents —Y—CH(R12)—COOH, —CHO, —CH═CH—COOH, or —COOR13 (Y represents a single bond, —CH2—, —CH(OH)—, —CO—, —CO—NH—, or —CO—NH—CH2—CO—NH—, R12 represents hydrogen atom or a lower alkyl group, and R13 represents hydrogen atom, —CH(R14)—COOH(R14 represents hydrogen atom, a lower alkyl group, or hydroxy group), —[CH2CH2—O]n—CH2—CH2—OH, —CH2—O—[CH2CH2—O]m—CH2—OH, or —[CH(CH3)—CO—O]p—CH(CH3)—COOH (m, n and p represent an integer of 1 to 100))], a salt thereof or an ester thereof, which has a property of being converted into a retinoid after absorption in vivo.
Novel 5α-reductase inhibitors: Synthesis, structure-activity studies, and pharmacokinetic profile of phenoxybenzoylphenyl acetic acids
Salem, Ola I. A.,Frotscher, Martin,Scherer, Christiane,Neugebauer, Alexander,Biemel, Klaus,Streiber, Martina,Maas, Ruth,Hartmann, Rolf W.
, p. 748 - 759 (2007/10/03)
Novel substituted benzoyl benzoic acids and phenylacetic acids 1-14 have been synthesized and evaluated for inhibition of rat and human steroid 5α-reductase isozymes 1 and 2, The compounds turned out to be potent and selective human type 2 enzyme inhibitors, exhibiting IC50 values in the nanomolar range. The phenylacetic acid derivatives were more potent than the analogous benzoic acids. Bromination in the 4-position of the phenoxy moiety led to the strongest inhibitor in this class (12; IC50 = 5 nM), which was equipotent to finasteride. Since oral absorption is essential for a potential drug, 12 was further examined. In the parallel artificial membrane permeation assay (PAMPA) it turned out to be a good permeator, whereas it was a medium permeator in Caco2 cells. After oral administration (40 mg/kg) to rats a high bioavailability and a biological half-life of 5.5 h were observed, making it a promising candidate for clinical evaluation.
CHEMICAL COMPOUNDS
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Page/Page column 126, (2008/06/13)
The present invention relates to novel compounds with a variety of therapeutic uses, more particularly novel substituted cyclic alkylidene compounds that are particularly useful for selective estrogen receptor modulation.
