Ppg-sipsy

Magainin Pharmaceuticals, Inc.

Michel Bulliard

William Alvin Kinney

Harold Meckler

Steven Jones

Meena N Rao

Blandine Laboue

Tony Pintus

Sonia Roussiasse

Xuehai Zhang

Nancy Lee

Yvon Derrien

A method for preparing pyrrolidine derivatives comprising cyclizing a compound of formula (I):in the presence of: a) a catalyst, b) a primary amine and c) a base, in a solvent to obtain pyrrolidine derivative of formula (II) below:

Cyclization method for the synthesis of pyrrolidine derivative compounds

A method for preparing a thiazolidinedione, oxazolidinedione or hydantoin compound of formula (I) from a compound of formula (II):wherein Q represents an oxygen atom or a sulfur atom; Q1 represents an oxygen atom or a sulfur atom; R1 and R2, which can be identical or different, represent a hydrogen atom, a Calkyl chain, a cycloalkyl, an alkylaryl, an arylalkyl; the alkyl, cycloalkyl, alkylaryl or arylalkyl groups being optionally substituted by an alkyl, an alkoxy or aryloxy, a halogen, a hydroxy, a sulfino, a sulfonyl, an amino such as NH, NHR, N(R), wherein R3 represents an alkyl, an alkoxy or an alkylcarbonyl, reacting a compound of formula (II) with formic acid, either as a hydrogen donor in a hydrogen-transfer reaction or as a solvent in a hydrogenation reaction, in the presence of a catalyst containing a transition metal to obtain a corresponding compound of formula (I).

Method for preparing compounds derived from thiazolidinedione, oxazolidinedione or hydantoin

Optically active chiral diphosphine ligands

A method is described for stereoselectively reducing an unsaturated alkyl ketone substituent attached to a fused ring base. In this method, the unsaturated alkyl ketone reacts with a chiral oxazaborolidine reagent. This reaction stereoselectively reduces the unsaturated alkyl ketone to an unsaturated alkyl alcohol. The unsaturated alkyl alcohol can be further reduced, if desired, to produce a saturated alkyl alcohol. The fused ring base can be, for example, a steroid ring base or a base of a vitamin D analog. The process in accordance with the invention can be used with an alkeneone substituent (e.g., a 22-ene-24-one substituent) or an alkyneone substituent (e.g., a 22-yne-24-one substituent) on a steroid ring base to make squalamine or other useful aminosterol compounds and intermediates for making aminosterol compounds.

Stereoselective synthesis of 24-hydroxylated compounds useful for the preparation of aminosterols, vitamin D analogs, and other compounds

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Angers, France

Michel Bulliard