91909-16-9

Upstream product

• 5407-98-7 1-cyclobutyl-1-phenyl-methanone 
• 70277-75-7 lithium acetylide 
• 4301-14-8 acetylenemagnesium bromide 

Downstream Products

• 135134-16-6 1-cyclobutyl-1-hydroxy-1-phenyl-2-propanone 
• 136722-66-2 1-Cyclobutyl-1-phenyl-1-trimethylsilanyloxy-hex-5-yn-2-one 
• 136722-08-2 1-Cyclobutyl-1-hydroxy-1-phenyl-7-ethylamino-hept-5-yn-2-one 
• 136722-48-0 1-Cyclobutyl-1-hydroxy-1-phenyl-7-(N-ethyl-N-methylamino) hept-5-yn-2-one 
• 136722-65-1 1-cyclobutyl-1-phenyl-1-(trimethylsiloxy)-2-propanone 
• 136722-45-7 1-cyclobutyl-1-phenyl-1-hydroxy-7-dimethylaminohept-5-yn-2-one 
• 1420991-28-1 C₁₃H₁₂ 
• 1420991-30-5 C₁₃H₁₂O 

Relevant academic research and scientific papers

Reactions of propargyl compounds containing a cyclobutyl group induced by a ruthenium complex

Reactions of [Ru]Cl ([Ru]={Cp(PPh3)2Ru}; Cp=cyclopentadienyl) with three alkynyl compounds, 1, 5, and 8, each containing a cyclobutyl group, are explored. For 1, the reaction gives the vinylidene complex 2, with a cyclobutylidene group, through dehydration at C δH and CγOH. With an additional methylene group, compound 5 reacts with [Ru]Cl to afford the cyclic oxacarbene complex 6. The reaction proceeds via a vinylidene intermediate followed by an intramolecular cyclization reaction through nucleophilic addition of the hydroxy group onto Cα of the vinylidene ligand. Deprotonation of 2 with NaOMe produces the acetylide complex 3 and alkylations of 3 by allyl iodide, methyl iodide, and ethyl iodoacetate generate 4 a-c, respectively, each with a stable cyclobutyl group. Dehydration of 1 is catalyzed by the cationic ruthenium acetonitrile complex at 70 °C to form the 1,3-enyne 7. The epoxidation reaction of the double bond of 7 yields oxirane 8. Ring expansion of the cyclobutyl group of 8 is readily induced by the acidic salt NH 4PF6 to afford the 2-ethynyl-substituted cyclopentanone 9. The same ring expansion is also seen in the reaction of [Ru]Cl with 8 in CH2Cl2, affording the vinylidene complex 10, which can also be obtained from 9 and [Ru]Cl. However, in MeOH, the same reaction of [Ru]Cl with 8 affords the bicyclic oxacarbene complex 12 a through an additional cyclization reaction. Transformation of 10 into 12 a is readily achieved in MeOH/HBF4, but, in MeOH alone, acetylide complex 11 is produced from 10. In the absence of MeOH, cyclization of 10, induced by HBF4, is followed by fluorination to afford complex 13. Crystal structures of 6 and 12 a' were determined by single-crystal diffraction analysis. Copyright

1,4-di-substituted piperidine derivatives

This invention provides novel 1,4-di-substituted piperidine derivatives of the general formula ?I! STR1 and the pharmaceutically acceptable salts thereof, wherein: Ar represents a phenyl group or a five- or six-membered heteroaromatic group having one or two hetero atoms selected from the group consisting of an oxygen atom, a sulfur atom and a nitrogen atom in which one or two optional hydrogen atoms on the ring may be replaced by substituent groups selected from the group consisting of a halogen atom and a lower alkyl group; R1 represents a cycloalkyl group of 3 to 6 carbon atoms or a cycloalkenyl group of 3 to 6 carbon atoms; R2 represents a saturated or unsaturated aliphatic hydrocarbon radical of 5 to 15 carbon atoms; and X represents O or NH. These compounds have selective antagonistic activity against the muscarinic M3 receptors and can hence be used safely with a minimum of side effects.

1-Aryl-1-hydroxy-1-substituted-3-(4-substituted-1-piperazinyl)-2-propanones and their use in treatment of neurogenic bladder disorders

Compounds are disclosed having the formula (I): in which R1is a C1 to C12 alkyl, said alkyl being straight or branched chain, saturated or unsaturated, monosubstituted or unsubstituted, said substituents being selected from piperidine, pyrrolidine, morpholine, thiomorpholine or cycloalkyl of 3 to 7 carbons, a cycloalkyl of 3 to 9 carbons, a lower alkylcycloalkyl of 4 to 9 carbons, or a polycycloalkyl of 2 to 3 rings containing 7 to 12 carbons; R2is hydrogen, phenyl, phenyl singly or multiply substituted with halogen, hydroxy, lower alkoxy, methylene dioxy, nitro, lower alkyl or trifluoromethyl, lower alkyl, said alkyl being branched chain or straight, saturated, unsaturated, or cyclic and substituted or unsubstituted, said substituents being selected from thienyl, pyrrolyl, pyridyl, furanyl, hydroxy, lower alkoxy, or acetoxyalkyl wherein the alkyl group has 1 to 3 carbons, phenyl, phenyl substituted with halogen, hydroxy, lower alkoxy, lower alkyl, nitro, methylene dioxy or trifluoromethyl, Phis phenyl or phenyl para-substituted by halogen, lower alkyl, lower alkoxy or trifluoromethyl; and the pharmaceutically acceptable nontoxic salts thereof. The preparation of the compounds, pharmaceutical compositions containing them and their use in the treatment of neurogenic bladder disorder are also enclosed.

Analogues of oxybutynin. Synthesis and antimuscarinic and bladder activity of some substituted 7-amino-1-hydroxy-5-heptyn-2-ones and related compounds

Oxybutynin chloride [4-(diethylamino)-2-butynyl α-cyclohexyl-α-hydroxybenzeneacetate hydrochloride, Ditropan] is widely used for the relief of symptoms in neurogenic bladder. This is a result of its combined anticholinergic, antispasmodic, and local anesthetic activities. In a study directed toward development of agents possessing the beneficial properties of oxybutynin, but having a longer duration of action, a series of metabolically more stable keto analogues of the parent ester, i.e. substituted 7-amino-1-hydroxy-5-heptyn-2-ones along with some analogues and derivatives, was prepared and evaluated for in vitro and in vivo antimuscarinic action in guinea pig preparations. Several members of the series were potent antimuscarinics having a longer duration of activity than that of oxybutynin in a guinea pig cystometrogram model. On the basis of its in vitro and in vivo antimuscarinic activity, coupled with a 5-fold greater duration of action than that of oxybutynin, 1-cyclobutyl-7-(dimethylamino)-1-hydroxy-1-phenyl-5-heptyn-2-one (14b) was selected for clinical evaluation.

1-aryl-1-hydroxy-1-substituted-3-(4-substituted-1-piperazinyl)-2-propanones and their use in treatment of neurogenic bladder disorders

Compounds are disclosed having the formula: STR1 in which R1 is a C1 l to C12 alkyl, said alkyl being straight or branched chain, saturated or unsaturated, monosubstituted or unsubstituted, said substituents being selected from piperidine, pyrrolidine, morpholine, thiomorpholine or cycloalkyl of 3 to 7 carbons, a cycloalkyl of 3 to 9 carbons, a lower alkylcycloalkyl of 4 to 9 carbons, or a polycycloalkyl of 2 to 3 rings containing 7 to 12 carbons; R2 is hydrogen, phenyl, phenyl singly or multiply substituted with halogen, hydroxy, lower alkoxy, methylene dioxy, nitro, lower alkyl or trifluoromethyl, lower alkyl, said alkyl being branched chain or straight, saturated, unsaturated, or cyclic and substituted or unsubstituted, said substituents being selected from thienyl, pyrrolyl, pyridyl, furanyl, hydroxy, lower alkoxy, or acetoxyalkyl wherein the alkyl group has 1 to 3 carbons, phenyl, phenyl substituted with halogen, hydroxy, lower alkoxy, lower alkyl, nitro, methylene dioxy or trifluoromethyl, Ph is phenyl or phenyl para-substituted by halogen, lower alkyl, lower alkoxy or trifluoromethyl; and the pharmaceutically acceptable nontoxic salts thereof. Pharmaceutical compositions containing the compounds and methods for the treatment of neurogenic bladder disorders are also disclosed. In the preferred compound Ph is phenyl, R1 is cyclobutyl and R2 is benzyl.