Lundbeck Pharmaceuticals, Italy

F.i.s. Fabbrica Italiana Sintetici S.p.a.

H. Lundbeck A/s

Pfizer Corporation

Mariano Stivanello

Carla De Faveri

Florian Anton Martin Huber

Riccardo Motterle

Florian Anton Huber

Antonio Ricci

Ennio Grendele

Alessandro Falchi

Juan C Colberg

Roberto Bortolaso

Federico Della Negra

Cristiano Grandini

Samuela Zambelli Franz

Ricci Antonio

The present invention relates to a non-hygroscopic salt of the compound 2-(3-(4-propylheptyl)morpholino)ethan-1-ol having the INN name delmopinol. In particular, the invention relates to the citrate salt of delmopinol. The present invention also relates to pharmaceutical compositions comprising the citrate salt of delmopinol depicted below. 

Salt of delmopinol

The present invention relates to a new process for producing intermediates useful in the manufacture of 2-(3-(4-propylheptyl)morpholino)ethan-1-ol. The invention also relates to intermediates 1-chloro-4-propylhept-3-ene and 1-iodo-4-propyl-hept-3-ene.

Method for the manufacturing of delmopinol intermediates

The present invention relates to a new process for producing 2-(3-(4-propylheptyl)morpholino)ethan-1-ol with the INN name Delmopinol. The invention also relates to three key intermediates 1-chloro-4-propylhept-3-ene, 1-iodo-4-propylhept-3-ene and 2-(3-(4-propylhept-3-en-1-yl)morpholino)ethan-1-ol.

Method for the manufacturing of delmopinol

The present invention relates to a method for the manufacture of 2-(3-(alkyl or alkenyl)morpholino)-ethan-1-ols by reduction of 8a-(alkyl or alkenyl)hexahydrooxazolo[2,3-c][1,4]oxazines encompassing a process for producing 2-(3-(4-propylheptyl)morpholino)ethan-1-ol with the INN name delmopinol. The invention also relates to 1-chloro-4-propylhept-3-ene, 1-iodo-4-propylhept-3-ene, 8a-(4-propylheptyl)hexahydrooxazolo[2,3-c][1,4]oxazine, 8a-(4-propylhept-3-en-1-yl)hexahydrooxazolo[2,3-c][1,4]oxazine and 2-(3-(4-propylhept-3-en-1-yl)morpholino)ethan-1-ol which are intermediates in the delmopinol process.

Method for the manufacturing of 2-(3-(alkyl and alkenyl)morpholino)-ethan-1-ols

The present invention relates to a method for the manufacture of 2-(3-(alkyl or alkenyl)morpholino)-ethan-1-ols by reduction of 8a-(alkyl and alkenyl)hexahydrooxazolo[2,3-c][1,4]oxazines encompassing a process for producing 2-(3-(4-propylheptyl)morpholino)ethan-1-ol with the INN name delmopinol. The invention also relates to 1-chloro-4-propylhept-3-ene, 1-iodo-4-propylhept-3-ene, 8a-(4-5 propylheptyl)hexahydrooxazolo[2,3-c][1,4]oxazine, 8a-(4-propylhept-3-en-1-yl)hexahydrooxazolo[2,3-c][1,4]oxazine and 2-(3-(4-propylhept-3-en-1-yl)morpholino)ethan-1-ol which are intermediates in the delmopinol process.

Methods are provided for the synthesis of key intermediates for the synthesis of Argatroban monohydrate, ethyl (2R,4R)-1-[(2S)-2-amino-5-[[imino(nitroamino)methyl]amino]-1-oxopentyl]-4-methylpiperidine-2-carboxylate compounded with HCl. Such intermediates are also provided.

Process intermediates and methods for the preparation of process intermediates for the synthesis of argatroban monohydrate

The present invention relates to an improved process for recovery of nalmefene hydrochloride[17-(cyclopropylmethyl)-4,5-alpha-epoxy-6-methylenemorphinan-3,14-diol hydrochloride] from an aqueous composition containing nalmefene and certain impurities.

Process for recovery of nalmefene hydrochloride

The present invention relates to an improved process for producing naltrexone[17-(cyclopropylmethyl)-4,5&#x3b1;-epoxy-3,14-dihydroxy-morphinan-6-one] from noroxymorphone[4,5-&#x3b1;-epoxy-3,14-dihydroxy-morphinan-6-one] by alkylation with a cyclopropylmethyl halide.

Method for the manufacturing of naltrexone

It is the object of the present invention a process for the preparation of 4-methyl-N3-[4-(3-pyridinyl)-2-pyrimidinyl]-1,3-benzenediamine and analogues thereof, intermediates useful for the synthesis of Imatinib, or 4-[(4-methyl-1-piperazinyl)methyl]-N-[4-methyl-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]phenyl]benzamide.

Process for the preparation of intermediates useful in the synthesis of imatinib

A process for the preparation of 4-methyl-N3-[4-(3-pyridinyl)-2-pyrimidinyl]-1,3-benzenediamine and analogues thereof, intermediates useful for the synthesis of Imatinib, or 4-[(4-methyl-1-piperazinyl)methyl]-N-[4-methyl-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]phenyl]benzamide.

Process for the preparation of imatinib and intermediates thereof

The present invention relates to a synthetic method for terbinafine and analogues thereof using metal catalysts, preferably Ni(II) salts and/or complexes.

Process for the synthesis of terbinafine and derivatives thereof

The present invention relates to chiral N-acetyl-alpha-amino acid salts of optically active &#x3b2;-amino alkylnitriles, and also to a process for preparing optically active &#x3b2;-amino alkylnitriles by resolving racemic &#x3b2;-amino alkylnitriles using chiral N-acetyl-alpha-amino acids as resolving agent.

Resolution of 3-amino alkylnitriles

This invention offers a process for the synthesis of a compound of the formula ##STR1## wherein R' is a phenyl, a substituted phenyl, a heterocyclic aromatic group, a heterocyclic aromatic substituted group, a linear or branched alkyl group, or a cycloalkyl group. The invention also comprises the following compounds of a formula 1' and 2' as useful new synthesis intermediates. ##STR2## wherein R is a phenyl, a substituted phenyl, an alkyl, a cycloalkyl and X is Cl, Br, I, F, CH.sub.3 SO.sub.3, p--CH.sub.3 --C.sub.6 H.sub.4 --SO.sub.3.

Process for the synthesis of 1,7-diarly or heteroaryl-heptane-4-ols and

The present invention relates to a process for preparing [R-(R*,R*)]-5-(3-chlorophenyl)-3-[2-(3,4-dimethoxyphenyl)-1-methyl-ethyl]- oxazolidin-2-one of Formula (1), characterized in that said process comprises the step of reacting (R)-3, 4-methoxy-amphetamine of Formula (3), with (R)-3-chloro-mandelic acid, of Formula (9): ##STR1##

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Schio, Italy

Mariano Stivanello