Lonza Inc.

Bristol-Myers Squibb Compnay

Aleksander Warm

Erick Moran Carreira

Nicka Chinkov

David Laffan

Jacques Gosteli

John McGarrity

Felix Previdoli

Gareth J Griffiths

Meinrad Brenner

Gary Ryan

Miriam Lorenzi

Lothar Zimmermann

The invention is directed to a process for the preparation of a cyclic carbamate starting with o-aminobenzyl alcohol and/or a suitable salt thereof, which is reacted with a cyclization agent selected from phosgene, diphosgene, triphosgene and mixtures thereof, and in that the reaction carried out in the presence of an aqueous base, and a water-immiscible organic solvent, said organic solvent mainly comprising at least one compound selected from C-alkyl C-carboxylates and mixtures of at least one C-alkyl C-carboxylate with at least one C-alkane.

Process for the synthesis of cyclic carbamates

The invention is directed to a process for the preparation of a cyclic carbamate starting with a chiral propargylic alcohol and/or a suitable salt thereof, which is reacted with a cyclization agent selected from phosgene, diphosgene, triphosgene and mixtures thereof, and in that the reaction is carried out in the presence of an aqueous base, and a water-immiscible organic solvent, said organic solvent mainly comprising at least one compound selected from C-alkyl C-carboxylates and mixtures of at least one C-alkyl C-carboxylate with at least one C-alkane. Another aspect of the invention is directed to a process for the synthesis of said cyclic carbamate starting described above, wherein also a process for the preparation of the chiral propargylic alcohol is provided.

An autocatalytic process for the synthesis of chiral propargylic alcohols.

Autocatalytic process for the synthesis of chiral propargylic alcohols

A process for the preparation of the compound of formula 

Process for the synthesis of a propargylic alcohol

A process for the production of substituted vinylbenzenes of the general formula: ##STR1## wherein R is a lower alkyl group having 1 to 4 C atoms, R.sub.1 is hydrogen or an acetyl group and R.sub.2 is hydrogen, a lower alkyl group having 1 to 4 C atoms or a benzyl group. A trialkylhydroquinone is cyclized with an aldehyde to an acetal and the latter is pyrolized to the end product. The substituted vinylbenzenes are valuable intermediate products in the synthesis of antioxidants.

Process for the production of substituted vinylbenzenes

A process for the production of substituted vinylbenzenes of the general formula: ##STR1## wherein R is a lower alkyl group having 1 to 4 C atoms, R.sub.1 is hydrogen or an acetyl group and R.sub.2 is hydrogen, a lower alkyl group having 1 to 4 C atoms or a benzyl group. A trialkylhydroquinone is cyclized with an aldehyde to an acetal and the latter is pyrolized to the endproduct. The substituted vinylbenzenes are valuable intermediate products in the synthesis of antioxidants.

A process for the production of 1-(N-methanesulfonyl-N-methylaminosulfonyl)-3-(2-pyrimidyl) urea derivatives (MMSPH). In the process, methanesulfonylmethylamine (MMSA) is first converted with chlorosulfonylisocyanata (CSI) into a 1-methanesulfonyl-1-methyl-3- (N-methanesulfonyl-N-methylaminosulfonyl) urea derivative (MMMSH) and then the MMMSH is converted with a 2-aminopyridine into the end product.

Process for the production of

A process for the production of 1-(N-methanesulfonyl-N-methylaminosulfonyl)-3-(2-pyrimidyl) urea derivatives (MMSPH). In the process, methanesulfonylmethylamine (MMSA) is first converted with chlorosulfonylisocyanate (CSI) into a 1-methanesulfonyl-1-methyl-3-(N-methanesulfonyl-N-methylaminosulfonyl) urea derivative (MMMSH) and then the MMMSH is converted with a 2-aminopyridine into the end product.

The following intermediate compounds, namely, 4-Oxo-3-(2-propenyl)-piperidine-3-carboxylic acid ester of the formula: ##STR1## wherein R is hydrogen, a formyl group, an acetyl group or a benzoyl group or is a benzyl group, whose aromatic ring optionally is ring-substituted by at least one halogen atom, and R.sub.1 is an alkyl group with 1 to 4 C atoms. 4-Oxo-3-(2-propenyl)-piperidine of the formula: ##STR2## wherein R is hydrogen, a formyl group, and acetyl group or a benzoyl group or is a benzyl group, whose aromatic ring optionally is ring-substituted by at least one halogen atom.

Process for the production of 4,5,6,7-tetrahydrothieno-[3,2-c]-pyridines

Substituted thienylethylamines of the formula: ##STR1## wherein R is formyl, acetyl or benzoyl or is benzyl, which is ring-substituted by at least one halogen atom, and R.sub.1 is lower alkyl, phenyl or substituted phenyl, are initial products for the production of antithromobolytically effective pharmaceutical agents. A process for the production of the above-mentioned compounds from substituted ethanolamines by their reaction with strong bases, further reaction with the resultant aziridines with 2-thienyllithium, and conversion of the resultant thienylethylamines with compounds of formula RX, wherein R has the above-mentioned meaning and X is a halogen.

Substituted thienylethylamines and process for their production

Substituted thienylethylamines of the formula: ##STR1## wherein R is formyl, acetyl or benzoyl or is benzyl, which is ring-substituted by at least one halogen atom, and R.sub.1 is a lower alkyl, phenyl or substituted phenyl, are initial products for the production of antithrombolytically effective pharmaceutical agents. A process for the production of the above-mentioned compounds from substituted ethanolamines by their reaction with strong bases, further reaction with the resultant aziridines with 2-thienyllithium, and conversion of the resultant thienylethylamines with compounds of formula RX, wherein R has the above-mentioned meaning and X is a halogen.

A process for the production of 4,5,6,7-tetrahydrothieno-[3,2-c]-pyridines of the formula: ##STR1## Thus, in the case of a 4-oxo-3-piperidine-3-carboxylic acid ester of the formula: ##STR2## an allyl group is introduced in the 3 position, the ester function in the 3 position is removed, the resultant compound of the formula: ##STR3## is ionized, reduced to the corresponding aldehyde of the formula: ##STR4## and with H.sub.2 S/HCl in the presence of a metal halide is cyclized to the end product. The synthesized compounds have antithrombotic action.

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Aleksander Warm